Very Long...sorry
Welcome!
JIB makes good points all around, so I'll drop in a few cents too(probably all it's worth).
You might consider a used bike with low mileage since you said you're not mechanically-inclined. The idea here is that your engine will already be broken-in which, from most accounts, is somewhat tedious and often involves a lot of fluid-changing, filter-checking and babying around for the first thousand miles or so. However, if you're okay with that sort of thing and you're anything like I was, you will quickly learn to enjoy tinkering around with the bike mechanically.
To address a few of your other questions: You might also want to think about waiting until you get through your MSF class before you purchase. The classes usually have a smattering of Rebels, GZs and other 250cc bikes (although I doubt any Hyosungs), and you can probably get a good feel for each of them there, with a (hopefully) knowledgeable instructor that will answer a lot of your questions. If you're impatient or you found a good deal on a bike you're considering it right now, then you should at least take a day or two, go to a couple of dealerships and sit on some (new or used), and get a feel for the controls, pegs, height and balance. It won't be as good of a test run as your class will be, but it could definitely narrow down your choices.
As far as outgrowing your bike is concerned, that really depends on what you get out of the bike personally. You sound like a pretty frugal sort of guy (not an insult, I'm that way too), and you may actually want to get another bike after a few months/seasons. But, like me and many others around here, you could wind up wanting to keep the 250 around for the mileage and so you can take your time shopping for a 600-800cc bike. You'd still like the 250 because it gives a unique feeling riding a smaller-class, quieter bike that's cheaper to work on than many other larger bore cycles, and frankly, more fun in some cases.
I doubt you'll have a problem with the hill you describe on the GZ at that speed. 25mph is about at the first-to-second gear transition (depending on your oil/sprockets/throttle/blah/blah/blah) and you'll have plenty left after that. Now if the hill was posted 45 or 55, you could be disappointed, but that would be with any 250, not just the GZ.
Try not to compare getting or upgrading a bike to changing cars. It's really not the same. JIB made a good point about the application of power in a car compared to a bike, and it's distinctly different. Power/weight ratios in cars are a lot closer than in motorcycles. The gradual opening of throttle will seem to have a MUCH greater effect on the feel of the bike since there are so many other physical variables in the equation (balance, vibration, wind, etc.). In a car, that all does truly affect it, but it rarely affects you, the driver, which means that those variables can distract that much more and if you're not ready, not expecting it, and most certainly lacking respect for it, it will (as JIB said) "get messy, and fast".
Be careful and keep frugal in your choices. Just because you're spending only around $2000 on a bike, doesn't mean you shouldn't treat it like a $50K car purchase. You've done half the work already by gathering information before you take the leap. You're ahead of most folks already, including some on this very msg board!
Also remember that this, and all advice has been given on a generally anonymous posting on an Internet message forum, take it for that it's worth.
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]I am hiding in Honduras. I am a desperate man. Send lawyers, guns and money. The shit has hit the fan.
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