Re: Do I get back in the game...?
4-stroke for dependability, 2-stroke for modibility. I keep my bike in my apartment, but I have a car otherwise so the bike is never out of my sight if it's outside.
As for your budget, if you were to get a 2-stroke and do some simple things to it you'd have an easy cruising 35mph machine and still have a hundred bucks left-over if you bought a bike as well. Lots can be done for free on these things to increase power output. As for 4-strokes I have never had one so I am pretty bias.