I've been playing on Windows 8 (it's a new computer, not built from scratch.) EVE plays completely fine. I do disconnect occasionally, but that's due to the internet setup being unstable at times. Thankfully has only happened when I've been in space (and I was right outside a station). All other times I've just been docked up. It's such a weird issue with this powerline adaptor. The easy fix is to just run up two flights of stairs, unplug it, then plug it back in again (doing the same to the local one near the feeding the computer doesn't seem to work - only the source being fed from the primary line does it.) I dunno if it's just a problem with that set of adaptors or the internal wiring somehow.
The other side effect is that the internet speed is greatly degraded compared to the source. I get maybe 7-9Mb/s downstairs compared to the 40-50 upstairs. Oddly enough, the upload speeds don't seem to change. Anyway I digress.
Windows 8 is mostly fine compared the the trouble you're having if you can't figure it out. There's a program (which is free?) that I believe is called "Classic Shell" which makes it functionally the same. With that going, there's not much real difference.
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Oh, and I'd definitely recommend trying out a Rokh first. You might not be picked up as much as the Vindicator, particular during prime times, but once you get in a few times with the ISK flowing and are comfortable with how things are run, you can easily transfer any more expensive modules you might have installed to the pirate hull. Also it would look a little silly (though not necessarily poorly fit) if your 1+bil Vindicator hull is only fit with T2 and Meta modules.
So basically:
Rokh Basic Fit --> Occasional Fleet, $$ --> Blinged Rokh (at least damage mods) --> More common pickup, $$$ --> Vindi --> Reliable Pickup, $$$$ --> Blinged/T2 Gun Vindi --> Fleets whenever (including ISN), $$$$$$
If/when you're done with the Rokh, you can contract it out with the pre-installed rigs or sell it on the market. Otherwise keep it as a backup asset, possibly use it for something else.
Long post, phew! But this is my only real outlet to discuss EVE, so you know.