I've owned a lot of two strokes in my time, and I do 90% trail riding and 10% moto. Trail riding is much easier on a two stroke engine than moto, in my opinion. Generally speaking, a trail rider rarely revs the engine hard for extended periods of time, while a guy who motos is usually wringing out the engine hard the entire time.
That being said, I never kept track of the number of hours I put on a top end. Our rule of thumb was to change the top end once per year. Using this time-line, I've never blew up an engine and I've never pulled a piston out that was cracked or marred in any way. If I had to make a guesstimate, I would say I put on approximately 120 hours on an engine per year.
Unless the seller can produce receipts to prove they very recently replaced the top end, I always put a new top end in a used bike first thing for several reasons:
1) Can't trust the previous owner kept accurate track of the number of hours on the engine.
2) Can't trust the previous owner cleaned the air filter correctly and on a regular basis.
3) Better safe than sorry. A sleeved/new cylinder and possible bottom end isn't cheap, especially after shelling out a few $grand$ for a "new to you" bike.
4) It helps you to keep track of your maintenance hours from a clean slate, with a bike you know is properly prepped.
Again, I'm not a moto expert; but If I were a moto guy I would not go past 75 hours of engine run time before I replaced the top end.