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I had an iPad 1 and maybe its the stress from College or something, but my new iPad is just fine. I use it and all, but I don't really think of it as a huge leap. I'm not wowed or something. Its faster and more useful, yes but I use it as much as I used to use my iPad 1. Mainly for college note taking and homework stuff, otherwise I'm using my Mac more often.
 
I think you need to put things into perspective. Think about a MacBook refresh that takes place year over year. Do two year old Macs seem all that inferior to new ones? Not as big of leap as the new iPad is over its original model. It's not even close internally and with apps that demand more resources it makes the new iPad all that much better to handle.
 
It's a gigantic upgrade for me coming from the iPad one. The new iPad just blows the old one out of the water, it's so much faster and the screen is insane. The dictation is amazing, I honestly didn't think it would be this accurate. In addition, the text on the screen is so much easier to read which makes browsing the web a breeze.
 
I'm not concerned with the iPad 3 being slowed down by any future upgrades because of the 1GB of ram. This is nearly twice the amount of the iPad 2 and much more than the original, it has what it needs to push all those pixels for a long time to come. I think waiting for the 4 at this point if you have an original is just silly.
 
Here is my response to your questions....
Considering you'll never miss the thinner/lighter iPad2 your new iPad is a pretty big leap. I have a few questions!

Do you notice the speed improvements?

Yes, everything is running faster, opening faster, apps not crashing from memory issues etc...

How are you liking the new Safari performance?

Not sure but I hated web browsing on ipad1 because of tabs always reloading. Now it seems I can have at lease 4-5 tabs and they hold their content so I can switch. Also page loading (all over wifi on same network as before) is now what I expect from my OSX Macs. Therefore, I have started to enjoy web browsing and with the Retina display I've found I can easily browse in portrait orientation which I like a lot.

Are there still grumbles you have from the original iPad that apple have yet to solve?

Slow charging, and this one is even slower!!! But of course that is expected. I'm just used to my MacBook Air and iPhone4 charging up in an hour or two, not like 6-8hrs or not charging while using apps.

Are you happy that you skipped iPad 2?

Yes, although I feel I would have solved a lot of my ipad1 headaches with ipad2 but I really don't want a new one every year. 2014 ipad5 here I come!

Was the upgrade worthwhile?

Yes, I'm very happy and have no real complaints except for the long charge times and not being able to charge while working on it.

Do you think you're likely to skip more than one more generation of iPad before jumping back in?

I will almost certainly skip ipad4 and will see what ipad5 brings. I think that the problem is new apps and iOS starts to get really slow once your 2 gens out so probably have to upgrade every 2 years if you want to keep upgrading iOS also and of course new apps. iphoto doesn't work on ipad1.

Any other thoughts/opinions you want to share?
 
One big improvement for me is that you can finally read every web page in portrait mode and the text is totally legible. Im also very impressed with iPhoto, a great app that wouldnt be doable on the first iPad, works well enough on iPad 2 but comes into it's own on the iPad 3.
 
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