Just my opinion. Take that for what its worth, along with a buck, and you can get a cup of coffee at Dennys.
If you LIKE crotch rockets, go for it. I had a 500 Ninja until very recently and it was a great bike. Its gone now, mainly because I didnt like twisting myself into a pretzel (not easy to do when you are overweight and have stiff joints from previous accidents). Younger and lighter folks seem not to have that problem though. If you do go with one, I'd stay away from the 250 and go straight to the 500. Tons of used 500s around, and the 250 just lacks any juice once you are moving. I know at least 5 guys here that had 250s. 3 of them sold after less than a year, and nobody saw 2 years of service out of one.
If the smaller "put around town" bike is all you want, go with a Rebel. I bought my son one. 200cc, very light, easy as hell to ride, nice and comfy. It does lack power at the top, but its not designed for long trips on the highway. Best of all, brand new ones start at $2k. You can find used ones for under $1k.
If you like the older 2 stroke styles, and you dont mind working on it all the time, then go for the one you picked out. I bought a '70 Yamaha 200 Twin that I puttered around with before I moved. It was alright. I carried a toolkit with me though, and always had my cell phone handy.