I will echo what others have said. All the basics of buying a used bike apply. If you're really interested in that year range 250 I'd spend a little while thumbing through the Wiki. I've owned mine since July and I've not once had to make a post asking a question here because between the Wiki and this forum nearly everything has been covered.
I opted to do just a couple of minor mods to mine. It is a 2006 and when I bought it it was sitting at 1,880 miles in great shape with a couple minor scratches. I figured resale wise it was better for it to be nearly stock than for me to do all the things I'd like. So I just installed an LED brake light bulb with a flasher, a cigarette lighter adapter for phone charging, and a RAM mount for my phone. But there is so much info on the Wiki you could nearly never stop working on it if you wanted.
Whatever you do, have fun!
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