deadguy,
This is one of those things that, in my opinion, is fairly subjective. We had two TW's a few years ago and, well, while they were fun little toys back then, they did not fit the bill for our intentions due to them being too small for decent street driving but did ok for mild off roading. But, that was several years ago. I've aged even more (duh!!) and, I have a Honda GL 1800 Goldwing for the street. But, I wanted something to zip around on for small runs here and there. Long story short, I started out looking at the Honda Monkey bike. Toooooooo expensive out the door. Next up, the Suzuki VanVan. Also too expensive out the door. Both of those have little to absolutely ZERO used ones anywhere. So, that left something I was familiar with, the Yamaha TW200.
I started looking and, within a couple days, I'd found plenty of them on C/L. We ended up getting an '07 with 582 miles on it. It had a rough younger life. The previous owners tore stuff off of it, laid it over on the right side and broke off the right rear turn signal and the hand brake lever. And there was more damage. But, I got it for about the best price possible and, I've been nurturing it back to life in the last week or so. It's now in SERIOUSLY better shape than it was. I'm awaiting a new stock rear sprocket and chain. I've already got the stock front one. It's way too low geared right now with a 60T rear sprocket. We'll see how much different it is with a set of stock gearing.
As for you and your intentions, well, remember, it's a fairly small bike, in terms of power and capabilities. Treat is as such, don't over use it, enjoy what IT will do for you within its realm of strengths, and you'll have a ball on it. I'm 66 years old and 6'2 1/2" tall and 240 lbs and, so far, I'm tickled with what it does with me on it. I've not done any off roading and don't plan on heavy duty off roading but, will occasionally scoot around on one or two of our local trails. If you cruise on over to youtube, you'll see all kinds of stuff about the infamous TW, riding it, working on it, modifying it, comparing it to the VanVan and more. Good luck.
Scott