Like you I hated Windows 8, but 8.1 was better and after a few hours navigating the OS I've gotten to where I just love the convenience it offers. It's "meh" on a desktop or large laptop where you do not use touch, but Win 8.1 is brilliant on a tablet.
The only thing about the original Pro and Pro 2 is the screen size. For any serious productivity I plug the display port adapter into an HDMI port (easy at most hotels we go to). Then you've got a TV sized monitor and you can play your movies (I like documentaries on classical economics).
Here's where I check for deals ... although there are bunches of sites like this:
Computers Deals | Slickdeals
Now that I've spent some time with the Surface Pro, it appears to be well worth the retail $1,000'ish asking price. MS product support on the Surface is astonishing. Walk in with a gripe, walk out with a new unit (YMMV). MS has been able to optimize memory and storage in such a way as to make your Surface do everything a home PC can do, yet load the OS and software faster than your Android tablets. It's a cool tool.
I am sure there will be some hot Thanksgiving (Black Friday) deals if you can wait until then.
There is nothing wrong with the original Surface Pro ... the battery life is about half of the real world time you will get on the Pro 2, but if you get a battery cover that makes it as long lasting and it is actually faster.
The Pro 2 is IMHO a "sweet spot" if you can find one under $500. With the profit sharing check a Pro 3 could be a "why not" purchase.
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Some smart Delta pilots who had this system figured out and working approached the Company and were told "thanks but, no thanks." I'm not sure Delta really wants any line swine input on our EFB.