I am not really an experienced 2-stroke mechanic, but I am interested and have done some reading. I don't think all 2-strokes need this much work to replace crank seals, but many multi-cylinder machines do...just make sure and check out the situation before buying. Basically, if the crank seals leak, gear lube, crankcase oil, and/or most importantly air can leak into the cylinder, fouling and/or leaning out the mixture. If oil is getting in you will have detonation, which will lead to a hole in your piston. If air is getting in it will run lean, just like a 4 stroke, but 2-stroke are much more susceptible to seizure from overheating as they are much more reliant on the correct fuel mixture to cool the piston (cuz there is no oil, except what's contained in the gas!) The nice thing is a 2-stroke engine rebuild can be done in 1 long afternoon, as there is no valve train. I think the going rate for a crank rebuild is right around $500, so if you get something that needs it, you are probably screwed...and it is my understanding that just as many old neglected 2-strokes need crank seals as old neglected 4 strokes need new carb boots. Google USA 2-strokes or 2-Stroke World for forum info.
There was an annual benefit ride/race around Lake Erie going several years ago that was limited to 250cc. I do not if it is still going on, but several guys did it on 2-strokes in 8-12 hours, so I think what you want to do is do-able. You are just gonna have to do more specific research on your own and get familiar with 2-strokes in a hurry.