Buy a service manual and do it yourself. Saves time and money. Just being honest. I do all my own maintenance just because I don't trust any mechanic anymore after some of the horror stories I've gone through. About the only thing I can't do on a bike is replace a tire and that's only because I don't have the equipment to do it. I could use blocks and a 2x4 but nah. I'll just take the wheels in and drop them off and pick them up later. Pre-purchase inspections are easy. Google can help on that or maybe one of your friends who knows motorcycles? I'd even possibly help out depending on the time/date.
As far as a 250 getting boring? Yeah, if you ride it in a straight line all the time. But I have as much fun on a properly setup 250 in the lakes backwoods on 113 or at BIR. Just as much, if not more fun as I have on my ZX10 in the same places. Ultimately up to you. The 250 will peter out at around 80 MPH so if you're planning on taking it on the interstate bad choice especially if you're bigger. Go for the new Ninja 300 it will get up to 120 now. Or for a 600 as stated earlier. It all depends on how big you are. The SV650 is one of my all time favorite bikes as I used to have a race bike that was converted from an 01. That thing was a riot. Handled like a dream and was a terror on the track although not very competitive on the straights it could easily overtake a lot of the bigger bikes in the curves. On the street it was enough to commute and have fun in town. The Ninja 650R is a pretty good bike too. Has the sportbike look but a bit more relaxed riding ergos. It too is a 650 twin and is quite fun to ride (I looked at getting one years ago).
But, if you're set on a 250R, go 08+ since they redid the suspension design for the better on them. If you look at all the bikes in the N250 class at BIR they are all 08+. If you can, go for the Ninja 300 but if you're a bigger guy, as I am, look at something with a bit more power like the SV650, 650R. They aren't classified as sport bikes so insurance will be cheaper and they can be found cheap (especially the SV). The 636 Ninja (old ones or the new ones) is about the perfect street bike. More than enough power and it handles awesome. I had an 05 and have been looking to purchase another to make it a track bike. Only problem is with the 636s squids tend to stunt the shit out of them and beat them to hell so they usually require some work.
