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I bought my first MacBook Pro in Summer 2010. I used it through my entire 4 years of high school, I upgraded to a used Mid 2014 MBP 13" summer 2016)

First computer 2010-2016
Second computer 2016-present

I bought the base Mid 2010 MBP 13" 2.4GHz C2D. I upgraded the ram to 8GB, and then to 16GB. Went from the stock 250GB to 750GB and then a 512GB SSD. Great machine, but the hard drive cable failed and rather than spend $40, I decided I'd also like a new machine and bought a 2 year old used Mid 2014 MBP 13" 2.6GHz Core i5, 16GB ram and 128GB SSD. I'm planning on upping to a 256GB SSD soon though.

I'm really not looking forward to when I have to replace this machine. I'll have to buy a used machine but with 16 or whatever max ram it can be configured with along with a 512GB SSD.

I used to always want the one with the faster processor, but a few MHz and other features are probably a second or so faster, but does the slight increase in speed justify the cost?
 
I upgrade about every 3 years... started with a 2009 MBP.... 2012 Retina MBP... 2015 5K iMac... and 2018 13" tbMPB. I also had a 2013 or 2014 MBA for a while, but gave it to my grandson for high school.
 
I have a late-2013 CTO (fully specced up) at the moment and I don't think I'll be upgrading to a new model for years to come.
 
I think it really depends on whether or not the "one you have" is still running well and doing everything that you normally do on it without problems.

For some, an 8-year-old laptop may still satisfy those goals.
For others, a 3-year old model may be "falling behind".

6-7 years is about right for me.

I replaced my 2010 model (still looks great and runs fine) with a 2015 in December 2016. The 2016 MBP's had just been released, but I judged the 2015 model to be "the better buy" -- and boy, am I glad I made that decision!
 
I replaced my 2010 model (still looks great and runs fine) with a 2015 in December 2016. The 2016 MBP's had just been released, but I judged the 2015 model to be "the better buy" -- and boy, am I glad I made that decision!

the 2015 seems to be the most solid MBP of all. Ports, magsafe, no keyboard issues and can pretty much keep up with the newer models.
 
Every year or two, why? The longer you use your mbp, the lower the resale value it’s gonna be, so selling the last year that still has a high value of money and buy the newest is I think better than using your mbp until it’s worthless. You got to use newest tech and speed upgrade too when upgrading every year or two.
 
I ordered last week a 13' nTB, but my CC issued a fraud alert and so the order couldn't be processed. Which has now made me rethink and I'll let the order cancel itself.

I am currently using a late-2013 2.6 GHz i5 16GB 13". It's still amazingly snappy. My 2008 13' MBP is still functioning and my parents use it. Since it is getting very long in the tooth, I was going to do another hand-me-down. However, I will now wait to see if the nTB gets updated in the fall or wait till 2019, or buy a min-spec MB or Air for my parents. Main reason for the decision not to purchase is the nTB isn't updated at all and doesn't have the new 2018 keyboard. Also I'll miss my USB-A ports and SD-slot. I tend to be the type that wants to max out on specs, but the price is getting to be cray, especially for SSD upgrades....
 
just updated from 1st gen. MBA 2008 to the MBP 15" 2018. i expect to use it for another 10 years.
i did not do much work with the mac (but very much rely on iPad and iPhone), but the 1st gen. MBA is too old for me.
4 key questions before the purchase i DID consider:
> affordable? (how much is my budget?)
> valuable? (the new one fits all my work & some entertainment?)
> replaceable? (why mac but not other pc? or the function of a new mac can be separately replaced by other devices?)
> keepable? (i never sold any used apple products, i collected all of them, so i consider every new purchase very seriously)
 
Every five years or so. I really like the 2018 but I’ll likely wait for 802.11ax, which I imagine will be 2020. But I’m tempted. Really tempted.
 
Just move to my 2018 after 9 years with my last MBP. Over those years it did gain an extra drive, ram, new battery, replacement charging cables and an ssd.

I switch-out my iMac more frequently as it does more intensive task where performance matters.
 
Unless it breaks, I usually wouldn't consider it until I can get something at least twice as fast.

2007: dual 2.2GHz 15" MBP
2011: quad 2.2GHz 17" MBP
2018: hex 2.6GHz 15" MBP

As of this year, my 2011 started suffering from bad GPU solder disease. Luckily, the new ones are twice as fast, so I'm OK with the (somewhat forced) timing of the replacement.

I gifted my 2007 to my parents. After also gifting them a 250GB SSD, it fulfils their needs. Not sure what I'll do with the 2011 17", probably keep it around as a backup/media PC because the big screen is still glorious.
 
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10/2015 - purchased an iMac, later sold it on 09/2016 (sold it for $450 less than I paid)
11/2016 - purchased 13" nTB MBP... don't think I'll upgrade until the redesign. (currently valued at $847 less than what I paid for it. Similar drop off considering the two year difference.)
 
How often do you guys upgrade your macbook pros? I just got a new one for the first time in 9 years and know I waited too long. On my old one, I can no longer check gmail, safari barely works, and it's just ULTRA, ULTRA slow. So I need good advice on how to do this better next time.. I definitely won't wait 9 yrs... That's for sure.. What's your advice?

Still running my original 2012 15" rMBP.....had bought a 2016 when the TB came out and returned it after a week....still waiting on something to tempt me to buy a new one...so far nothing has....
 
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My late 2013 has been with me now for more than 5 years, and I have no intention whatsoever to replace it anytime soon. I don’t feel the inclination to upgrade so fast anymore.
 
I used to upgrade every single upgrade cycle... my latest MacBook Pro is the 2016 (first touchbar version) model and I haven't bothered updating since. I think I'll let the AppleCare run out on this one for the first time. There is really no compelling reason for me to upgrade. There isn't more storage, RAM, or that much faster CPU, and I already have an eGPU (Not to mention three other Macs).

There used to be compelling technologies, USB 3.0, Thunderbolt, Retina displays, quad core, etc.

Seems the only thing better about the new computer is hexacore that throttles.
 
I got tired of buying new PC's due to component failure (3 in 5 years time) and switched to my beloved MBP. I got my MBP non retina in 2012, have upgraded memory and swapped out the HD to SSD. I don't have any need to upgrade at the moment as it works great! That was my plan, to hang onto it for a while and thankfully it has worked.
 
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I recently upgraded my rMBP mid-2014 (2.8 Ghz, 8GB, 256GB) to a slightly younger rMBP early-2015 (2.7 Ghz, 16GB, 1TB). I did not anticipate the disastrous MBP-redesign and became aware of it only earlier this year when I started looking into upgrading my mid-2014 machine. Everyday tasks were still running buttery-smooth like on day 1, but the 8GB memory caused some stutter in large data sets and I was running out of space on my SSD. I quickly realised that I was not willing to pay a premium to give up ports (I use the SD-card slot almost every other day), Magsafe, acceptable keyboard quality and the overall reliability of a refined design.

At the point of my realisation, I could not find any new 13" rMBP early-2015, but believe me, I tried... I called up Apple resellers all over Germany, Austria and Switzerland for weeks. I would have gladly bought a maxed-out early-2015 despite it being no longer state-of-the-art, with Apple Care to make sure it's going to last till Apple moves on from this current, anorexic MBP design. Despite my failure to source a brand-new machine, I was lucky enough to find a 1-year-old barely used rMBP early-2015 at a great price. The processor is slightly slower than the one in my rMBP mid-2014, but I haven't noticed this in any of my tasks. However, I have felt a considerable boost from the 16GB RAM and the 1TB SSD is a god's end as it means that I have no longer to work with a permanently attached external hard drive. My rMBP mid-2014, I was able to sell for € 900 and the rMBP early-2015 set me back € 1200. So, my upgrade cost me € 300 in the end.

I'm sorry, Apple discarded the tried and tested rMBP design for its current joke of a pro-line. Of course, they need to further develop their products and can't stick with one design forever, but I feel the current Macbook-lines are mostly a step back, rather than a step forward. With this in mind, I don't see myself upgrading again until my current rMBP bites the dust.
 
How often do you guys upgrade your macbook pros? I just got a new one for the first time in 9 years and know I waited too long. On my old one, I can no longer check gmail, safari barely works, and it's just ULTRA, ULTRA slow. So I need good advice on how to do this better next time.. I definitely won't wait 9 yrs... That's for sure.. What's your advice?
I like to upgrade every 2 or 3 years depending on how much has changed as far as CPU advances, RAM and drive speed.
Mostly it depends on if I can afford it, sadly not able to buy new for the last few years, but got a great deal on a used 2015 MBP that's doing just fine.
 
Bought brand new 2008 2.4Ghz aluminium macbook in 2008. Installed ssd in 2010 and upgraded ram to 8gb. Still runs fine, but feels slow for my needs.
So, just ordered 2018 refurbished macbook pro with touch bar.
 
Used to upgrade more often, but a combination of using my phone/iPad more and computer upgrades getting less impressive, I think it's now every 5-6 years.

With MBPs, I've gone Early 2006 15" -> Late 2008 15" -> Early 2011 15" -> Late 2016 13".
 
I used to upgrade my computers after 5-6 years (though I ended up keeping my old 2009 MBP for more than 7), and that's in theory how long I plan to keep the 2018 model I just bought.

The issue is, I don't see the newer MBPs as the well-built tanks they once used to be. They are still excellent machines, but a nightmare to fix, every generation suffers from at least one critical issue, and I had to go through more Apple repairs/replacements in the last 2 years than in the previous 8 combined. Only time will tell, but I've grown a bit pessimistic about their long term reliability.
 
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