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I'd also like to recommend the 15-85mm out of that lot. I was in a very similar situation recently, but my budget was more like $400. The more I looked into the available lenses in my budget, the more I convinced myself that the extra bump to $500 for a used 15-85mm would be leaps and bounds above my other options.

I recently started playing with primes, but this lens is almost always on my camera. It's very versatile, solidly built and has very good IQ.

I will upgrade to a quicker zoom down the road, but this does the job for me now and probably for quite a while.
 
...
The primes are great, but not the most versatile for a "carrying around" lens.
The kit lens has served me well and continues to do so. But I'm considering upgrading in that department (meaning, a versatile lens that would be on the camera 90% of the time)....


Beginners always think this. You have not learned to use your feet. The 50mm is the perfect lens for most portraits on a crop-frame body.

One good exercise is to place just the prime lens on the camera then shoot with it all day or for several days. You might mess many shots you could have gotten but in the end you ail have just as many good shots no matter which lens you choose, you will just have different good shots. The purpose of the exersie is to learn to see like that lens. to learn what that lens is best at., to see a subject and know quickly where you will need to stand to get the subject, light and background. For many years the 50mm was the "kit lens" and that was all people used. They made fine photos back then, makebe even better ones than we make today.

With a zoom lens you don't learn to move the camera position, you get lazy. The correct way to use the zoom is to (1) move the camera relative to the subject to get the perspective you want, then (2) adjust the zoom for the angle of coverage you want. Almost every beginner skips step #1.

I'd say if you have not yet shot at least 1,000 or so frames with a lens do NOT buy another one. Wait.

Here is how to decide on a new lens: Look at your photo library. If you own three lenses then you should have thousands of images in there before you are looking for a 4th lens. So sort the photos by f-stop. Are many of them shop "wide open" if so then you could use a faster lens. But if so your shot are at f/8 or f/11 you don't need a faster lens. Now look at the ones you shot with the kit lens. All many of then at one end of the zoom range, either 18 or 55. If so then you can use either a longer of wider lens. But if you are mostly using 35mm then no. Next look at the light level, if shooting in low light in many shoots then an IS lens might help.

The other thing to do is look at what you think of as your best work. Look critically. How could these be better? Is there even an equipment problem. At this point I'd guess if you have an equipment problem it is with lighting and you could use light defusers, reflector cars, bounce flash or other better lighting technique in you "pepple shots" and likely in shots of small objects.

I did this analisys once and ended up with a stroboframe flip flash bracket
http://www.amazon.com/Stroboframe-Camera-Flip-Flash-Bracket/dp/B00009UTLU
I'm NOT saying to buy one of these but to LOOK AT YOUR WORK and based the next bit of gear on some IDENTIFIABLE problem

Find some photos you like on-line or in a book or magazine, shoot 100 frames in effort to copy that style, go home and select the best five. See how well you did compared to the professional images This gives you a goal and a standard to compare with. Copying the style of the master is how artists have learn for centuries. At some point you see your work could be better and you fix it. At this point almost certainly the "fix" will not require a new lens.

Shot about 100 frames keeping five at least once a week. Those 100 frames need to be all with the same goal, some "look" you are trying to capture. Run you full post processing work flow (whatever that is) on your 100 images, likely that is fist to select the 20 best and work with those then dowselect the best five and do more work with those and finally fine tune those five. Then look again at the model photo from the book and plan the next attempt.

That 50mm is really best for "street photography" because you don't waste so much time fiddling with the zoom ring. You see the subject and then have learned how to pick the spot you need to walk to. After a while you KNOW that spot without looking through the camera. The camera handles VEY fast with a fast prime, the AF works quick and you can most always work with a fast shutter speed and existing light. So you can have the shot just as fast you you get yourself to that spot. The key is learning to recognize where you need to be. And when things are moving it is learning where you will need to be in one minute.
 
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For the most part, if you've got enough stop to shoot with a zoom on FF, you can sacrifice that flexibility and shoot just as well with primes on crop, as fast primes are generally about two stops faster than fast zooms. But there are specific circumstances, some relating to low light shooting (anywhere you'd use a 50mm f1.2 or 24mm f1.4), for which FF is worth it and not easily replaced.
What you're saying is not necessarily correct in practice: first of all, you can't just equate a f/2.8 zoom with a f/1.4 prime. If you use your flash, then there is no substitute for a large aperture, because the aperture determines how far you can go when you balance background and foreground light. Moreover, if you shoot with lighter rangefinder-style camera (e. g. a Fuji X100s), you can handhold longer times than with a heavier dslr. (Yes, Leica has full frame rangefinder cameras, but these cost an arm, a leg and a firstborn. ;)) And lastly, sensor technology has progressed so far that you can use current-gen crop sensors at ISO 4,000 or so. They in fact handle noise much better than old full frame sensors. In essence, current-gen crop sensors are much, much better than just good enough. (Of course, the full frame sensors based on the same technology are still better, but you're really far in the territory of diminished returns.)

For low light photography specifically, I'd rather use my rangefinder-style X100s than my dslr with a f/1.4 prime.
 
Wow. Very detailed response. Thanks for taking the time.

Some very interesting points in there. While I get your point about the 50mm, and about moving my feet rather than the zoom, I still think that is not always possible. In fact, I'd say, that's a challenge in the majority of my use-cases.
That's not to say I shouldn't make more of an effort to physically move myself closer or further to take the shot. I certainly could learn a thing or two from that. But I have found that in my particular setting, where I live, the things I shoot, etc. That is more often than not, hard to do.
Street photography, yes, that makes sense.
I rarely do street photography.
Shots in my backyard, I certainly could move (and I do). In fact, those are the only times (and indoors) that I use my primes.
Beyond that, my photography is usually whatever vistas (sunset, beach, mountains, lake) that I have at my disposal in the area (I don't travel much at this stage). Given the area I live in and the demands made on my time (Job, family, etc.) I don't end up doing photography the way some do (drive to a nice location, go for a hike, etc), rather, I am presented with opportunities when I can steal some free time, and have to do the best I can with what's around me.
All this to say that "what's around me" (living in the suburbs, near a big city) is usually busy, traffic, obstructions, impassable, etc. Moving my feet is not always an option.

I still like your overall thoughts on how to approach things. Go over my existing collection of shots (and yes, I do have thousands) and see what I tend to gravitate towards...

Beginners always think this. You have not learned to use your feet. The 50mm is the perfect lens for most portraits on a crop-frame body.

One good exercise is to place just the prime lens on the camera then shoot with it all day or for several days. You might mess many shots you could have gotten but in the end you ail have just as many good shots no matter which lens you choose, you will just have different good shots. The purpose of the exersie is to learn to see like that lens. to learn what that lens is best at., to see a subject and know quickly where you will need to stand to get the subject, light and background. For many years the 50mm was the "kit lens" and that was all people used. They made fine photos back then, makebe even better ones than we make today.

With a zoom lens you don't learn to move the camera position, you get lazy. The correct way to use the zoom is to (1) move the camera relative to the subject to get the perspective you want, then (2) adjust the zoom for the angle of coverage you want. Almost every beginner skips step #1.

I'd say if you have not yet shot at least 1,000 or so frames with a lens do NOT buy another one. Wait.

Here is how to decide on a new lens: Look at your photo library. If you own three lenses then you should have thousands of images in there before you are looking for a 4th lens. So sort the photos by f-stop. Are many of them shop "wide open" if so then you could use a faster lens. But if so your shot are at f/8 or f/11 you don't need a faster lens. Now look at the ones you shot with the kit lens. All many of then at one end of the zoom range, either 18 or 55. If so then you can use either a longer of wider lens. But if you are mostly using 35mm then no. Next look at the light level, if shooting in low light in many shoots then an IS lens might help.

The other thing to do is look at what you think of as your best work. Look critically. How could these be better? Is there even an equipment problem. At this point I'd guess if you have an equipment problem it is with lighting and you could use light defusers, reflector cars, bounce flash or other better lighting technique in you "pepple shots" and likely in shots of small objects.

I did this analisys once and ended up with a stroboframe flip flash bracket
http://www.amazon.com/Stroboframe-Camera-Flip-Flash-Bracket/dp/B00009UTLU
I'm NOT saying to buy one of these but to LOOK AT YOUR WORK and based the next bit of gear on some IDENTIFIABLE problem

Find some photos you like on-line or in a book or magazine, shoot 100 frames in effort to copy that style, go home and select the best five. See how well you did compared to the professional images This gives you a goal and a standard to compare with. Copying the style of the master is how artists have learn for centuries. At some point you see your work could be better and you fix it. At this point almost certainly the "fix" will not require a new lens.

Shot about 100 frames keeping five at least once a week. Those 100 frames need to be all with the same goal, some "look" you are trying to capture. Run you full post processing work flow (whatever that is) on your 100 images, likely that is fist to select the 20 best and work with those then dowselect the best five and do more work with those and finally fine tune those five. Then look again at the model photo from the book and plan the next attempt.

That 50mm is really best for "street photography" because you don't waste so much time fiddling with the zoom ring. You see the subject and then have learned how to pick the spot you need to walk to. After a while you KNOW that spot without looking through the camera. The camera handles VEY fast with a fast prime, the AF works quick and you can most always work with a fast shutter speed and existing light. So you can have the shot just as fast you you get yourself to that spot. The key is learning to recognize where you need to be. And when things are moving it is learning where you will need to be in one minute.
 
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@Puckman
Regarding primes vs. zooms, I strongly, strongly suggest you consider primes. I used to think the same way you do, but the quality of your photos will improve, because with primes you learn better how to get the composition of a shot right. As a beginner, I'd look into getting a 28~35 mm (e. g. Sigma's 30 mm f/1.4 or Canon's 28 mm f/1.8). Primes of these focal lengths are relatively inexpensive and fast.
 
I am surprised no one has suggested an ultra wide lens. You seem to have the mid range covered, but are lacking at both extremes.

As you prefer landscapes and macro, I would suggest the Canon 10-22 EF-S. I had this on a Canon crop body for a couple of years and can highly recommend it.

The other option, and I would suggest this is a future purchase if not now, is one of the 70-200 F4 L's. Again I have had both is and non-is F4 L's and would highly recommend them both.

I would not get any other L lenses until you go FF. The crop body would not get the benefit of the better glass at the extremes. Where the L's excel is at the corners on a FF sensor. Crop sensors just aren't big enough to cover the full frame area projected by an L, therefore you are carrying round and paying for excess glass that camera cant even use.

Saying that about L's, if you are going full frame in the next year or so, or need the weather sealing, then go for L's anyway. Cost allowing of course. But bare in mind that a weather sealed lens is only sealed on a weather sealed body.

The most important thing though is stay away from the dark side! Canon all the way!
 
Primes:

I have the 28mm f/1.8 and the 50mm/f1.4, so to whoever is suggesting the primes, while I have tried to force myself to use those 2 more, I have found that it's not always handy to either switch lenses on the go, or always possible to move closer/farther to the subject. That is why I am looking for a walk-around lens.
When I'm at home, and can take my time swapping lenses or adjusting where I stand, then the primes are not a problem. But I wouldn't call them as versatile as a zoom lens for every day usage.

70-200L: That is on my radar, but further down the line. I'd rather get something like 17-55 first, then the macro 100, then maybe the 70-200L (That is my current thinking, btw).
 
Beginners always think this. You have not learned to use your feet. The 50mm is the perfect lens for most portraits on a crop-frame body.

One good exercise is to place just the prime lens on the camera then shoot with it all day or for several days. You might mess many shots you could have gotten but in the end you ail have just as many good shots no matter which lens you choose, you will just have different good shots. The purpose of the exersie is to learn to see like that lens. to learn what that lens is best at., to see a subject and know quickly where you will need to stand to get the subject, light and background. For many years the 50mm was the "kit lens" and that was all people used. They made fine photos back then, makebe even better ones than we make today.

With a zoom lens you don't learn to move the camera position, you get lazy. The correct way to use the zoom is to (1) move the camera relative to the subject to get the perspective you want, then (2) adjust the zoom for the angle of coverage you want. Almost every beginner skips step #1.

I'd say if you have not yet shot at least 1,000 or so frames with a lens do NOT buy another one. Wait.

Here is how to decide on a new lens: Look at your photo library. If you own three lenses then you should have thousands of images in there before you are looking for a 4th lens. So sort the photos by f-stop. Are many of them shop "wide open" if so then you could use a faster lens. But if so your shot are at f/8 or f/11 you don't need a faster lens. Now look at the ones you shot with the kit lens. All many of then at one end of the zoom range, either 18 or 55. If so then you can use either a longer of wider lens. But if you are mostly using 35mm then no. Next look at the light level, if shooting in low light in many shoots then an IS lens might help.

The other thing to do is look at what you think of as your best work. Look critically. How could these be better? Is there even an equipment problem. At this point I'd guess if you have an equipment problem it is with lighting and you could use light defusers, reflector cars, bounce flash or other better lighting technique in you "pepple shots" and likely in shots of small objects.

I did this analisys once and ended up with a stroboframe flip flash bracket
http://www.amazon.com/Stroboframe-Camera-Flip-Flash-Bracket/dp/B00009UTLU
I'm NOT saying to buy one of these but to LOOK AT YOUR WORK and based the next bit of gear on some IDENTIFIABLE problem

Find some photos you like on-line or in a book or magazine, shoot 100 frames in effort to copy that style, go home and select the best five. See how well you did compared to the professional images This gives you a goal and a standard to compare with. Copying the style of the master is how artists have learn for centuries. At some point you see your work could be better and you fix it. At this point almost certainly the "fix" will not require a new lens.

Shot about 100 frames keeping five at least once a week. Those 100 frames need to be all with the same goal, some "look" you are trying to capture. Run you full post processing work flow (whatever that is) on your 100 images, likely that is fist to select the 20 best and work with those then dowselect the best five and do more work with those and finally fine tune those five. Then look again at the model photo from the book and plan the next attempt.

That 50mm is really best for "street photography" because you don't waste so much time fiddling with the zoom ring. You see the subject and then have learned how to pick the spot you need to walk to. After a while you KNOW that spot without looking through the camera. The camera handles VEY fast with a fast prime, the AF works quick and you can most always work with a fast shutter speed and existing light. So you can have the shot just as fast you you get yourself to that spot. The key is learning to recognize where you need to be. And when things are moving it is learning where you will need to be in one minute.

What a useful post. I'd never thought about sorting my library by F stop or Lens setting. I will be certain to check that out before buying my next lens.
 
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My favorite crop walk around lens was the 16-35, which I sold when moving to FF. I also sold my other favorite, the massively under appreciated 60mm Macro (only $300 used!). No, you don't need to worry about selling your EFS (I sold my FF when moving to FF). No, you don't need FF to appreciate L. The special glass and coatings (what you're mostly paying for) come through on just about any sensor. No, you don't need primes to take good pictures. I've moved to all primes, but once you know how to move and how to create perspective, a zoom can provide that while still allowing the extra framing options the OP has already stated he needs. Yes, fast glass is awesome (i love my 1.2), the OP already has a 1.4 and knows what it can do and has decided for himself that zoom is more important. Its just a question of which zoom.

I've not tried it myself, but even dudes who've switched to FF like the 10-22 so much, they hack it to fit. It must do something good. Once you've picked out candidates, read on them here as a last step to deciding:

http://www.fredmiranda.com/reviews/showproduct.php?product=221
 
Reviving this week-old thread for an update.

Just wanted to let you all know that I'm leaning towards holding off on upgrading the camera body to FF for the time being.
Not really sure about spending good money on EF-S lenses (17-55 was the frontrunner), so instead, I'm leaning towards getting the EF 100 2.8 macro.

1) That will work if I do decide to go FF.

2) If I keep my 28/1.8 and 50/1.4 and add 100/1.8, I will now have a decent range covered by all prime lenses. Yes, it's more lens changing and won't give me the versatility of a nice zoom lens, but it will cover the range of the kit lens 18-55 and then add the 100 option for closeups, portraits, etc.

3) I have been wanting to try out macro. The 100 is a macro lens and will allow me to discover some new territory.

4) I will keep on practicing with what I have for the time being. I don't feel capable enough yet to know the limitations of my T3i or the understanding needed to decide if I should go FF or not.

Thanks for all who offered their advice.
 
3) I have been wanting to try out macro. The 100 is a macro lens and will allow me to discover some new territory.

Tamron recently released the 90mm macro with VC (vibration control/image stabilisation) for around $600 (Australian). If it's as good as the non VC version optically it's on par with the canon for a lot less $$$. ;)
 
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