Andre,
$8500 is a little pricey with very limited spares (really none, as jetting and sprockets are not spares). I would also try to get a feel for what amount of mileage is on the crank and top end.
Get as many detailed photo's as possible of the bike without the body work on it. You can tell by how clean a bike is as to how well it was maintained.
Honestly a GP bike should be nothing short of as it came from the factory in terms of cleanliness.
If I lived a little closer, and gas wasn't stupid expensive, I would make a run down and check it out for you. But that shouldn't stop you from asking for references on the bikes condition. I am sure he races, so there have to be other racers in the area who can give you some input on the bike. If he has raced USGPRU, talk to some of those members to see if they know him, how he prepares his equipment, as well as anything about this bike.
As for F2 with the AFM, this would be a good bike for that class (if it's in good shape). There are a good number of riders already running RS's so you should gave some support there in the club. Also, Roland Cushway in Vallejo knows these bikes inside and out, so you can get him to help you out for his bargain basement prices. THen there is Kevin Murray up at THill who knows 2-strokes.
No matter what you get, a GP250 bike is something that is amazing compared to an NSR. It's a whole new thing!
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Charles Gallant