A TW is a perfect bike if you want the best of both worlds in a short, maneuverable bike. If you're interested in this sort of thing, read up here a lot. Every motorcyclist has to know a bit more about maintenance than someone in a car, or they get rid of it. I guess there's the "have money" option but trailering a bike to pay someone to adjust your chain just sounds ridiculous to me. So read around on what it takes for bike upkeep.
If you're going to buy used, they're all decent, but try to avoid the 1987 model. It was the first year and their electrical system is unique to itself, so you end up having a hard time finding secondhand parts for them and end up paying too much for a new one.
Most importantly, look into the Motorcycle Safety Foundation and the courses they offer all over. You can pay for the course, in which you'll practice on a small bike (not uncommon to see the TW200 in the course) and learn a wealth of information to keep you safe. And you come out with your MC license.
So look into that and report back with any questions.