Last question first: at a certain point in your life, you might wind up with more disposable income than you have now. Some people spend money on cars or trucks, others on boats or tools... my hobby is guitars. I have five that I play regularly, three of them are worth upwards of $1000 each.
Plus, as you shop around, you're going to find out that there is a world of difference between a $200 "starter pack" guitar, and a $600 instrument; better materials and better craftsmanship translate to easier to play and far better sound. I've said it many times on this forum and others, and not everyone agrees with me, but take your time, and buy the best instrument that you can afford. If you can afford $250, that's fine-- just use it wisely. Decide what kind of music you want to play, what type of instrument fits that musical style, and then go out there and comparison shop. Hit every music shop you can reach, and play every instrument you can get your hands on. Haunt eBay and Craigslist, visit pawnshops.
What separates the various manufacturer's instruments from one another (outside of pricing) are sound and feel. Body size, shape and style, neck shape, fretboard raduis, size of frets, quality of workmanship, look... Once you get your hands on a few axes, you'll start to notice what's important to you in terms of feel. I happen to like hollowbody electrics for sound, with a slim D-profile neck, 12" radius fretboard and jumbo frets (which all points to Gretsch). In acoustics, I still like the neck profile, solid wood body with an "auditorium" shape over "dreadnought" and a strong low-end response (which pretty much all says Taylor). You will have to touch and play them to find out what speaks to you.
Where to buy? Wherever you find that special instrument. You will find it, and you WILL know it when you do.
In this economy, you may well find a good bargain in a used guitar; be sure to try it first. You can afford to be picky; waiting a little longer for the right instrument to come along simply means that you can save up more scratch to buy it when it does. Though when you speak of "seasoning" in an instrument, that is usually reserved for the so-called "vintage" market, which is going to be light years out of your price range. Don't get discouraged, and don't let some pushy salesperson sell you an instrument that your hands and ears don't think is right.
Oh yeah, welcome to Chordie!
"There's such a fine line between genius and stupidity."
--David St. Hubbins