Thumper's site will take you thru various options from just selling the parts to drop off the whole bike. They start at about $320 I believe if you send them your cylinder.
If you are the handy type, a local MC machine shop can bore your cylinder for about $60 and the piston kit from White Bros is $140. A shop manual is essential if you decide to do the work yourself and no special tools are required with the exception of a flywheel puller. On your '95 I believe the flywheel needs a mod, so you will have to send it out for modification or a core trade on a modded one. Thumper can take care of the flywheel.
The only way to keep it under $250 as you want to is to do ALL the labor yourself other than the boring and flywheel mod.
I did my '99 a few months ago. Not hard, but time consuming. Also lots of places where you can make errors, like dropping washers in the engine. Mine went off without a hitch, other than dropping a washer into the clutch side of the engine which required pulling the clutch side cover.
This is an easy project if you are a decent mechanic and have the right tools, like a GOOD torque wrench and the feeler gauges for setting the valves when done. A spare pair of hands come in handy for a few operations, like getting the cylinder back over the piston. If you can do a 2 smoke top end with confidence corrrectly, then doing the 280 is similar with the added complication of getting the cam back in right, dealing with the cam chain tensioner, and adjusting the valves.
OK, after re-reading your post I see you are in Cypress. If you decide to do it yourself, Kevin Stasny at K&S Cycles in Katy did my bore job. White Bros can sell you the stuff directly, or you can order it thru a local dealer as well that is hooked up with White Bros. If you are a TRH member, lots of dealers in the Houston area will give you 10% off parts and accessories.
If the do-it-yourself thing scares you, then you might want to get a labor quote from Kevin to do the top end for you. My guess is it would be $180-$250 in labor as it takes quite a bit of time to strip the bike down and pull the jug, then reassemble. While the head pipe is off I'd grind out the head pipe welds at the flanges. With the bike being a '95, you probably are due for a cam chain too. Heck, Kevin can get you the piston kit also and will probably be 10% off list. His work is very good - he was Colin Edwards' bike builder before Yoshimura picked him up and he still supports many a WERA rider.
Hope this helps,