Smoke is really no big deal, as long as its two stroke oil. If it starts burnin' crankcase oil, it is really no big deal either, until you know what else that means. What I'm trying to say is, its not likely that you are all the sudden gonna be burnin all of the crankcase oil from the bottom end, but it plays havoc with your jetting. It gives you rich symptoms, even though the jetting is correct. It could also pull air in, which is also bad for mixture.
I think you may just have a typical fat mixture while choking her to get it fired, if it stops. My bikes both smoke alot, until warm. They smoke less with better gas and perfect jetting. The best way to tell is the smell. A good two-stroke oil smells like you're at a race, but but if it starts being a lingering burnt plastic funky smell, then its the seals.
The school of thought is that it all depends on time on the bike, as to how often to rebuild. I agree with a few exceptions. If a bike sits too long it can be as bad or worse than a bike that gets rode on a regular basis.
In hillclimbing, I think people are rebuilding top-ends in the winter only. Of course the real fast guys do it twice a year. If you just ride for fun, I say a bike can go 3-5 years between rebuilds. Many guys will disagree probably, but once you get it right, it will haul for a long time.
Rebuilding the top-end is fairly simple, and manageable with a helper, but bottom ends require splitting the cases, that requires a special tool. When you get to the point that you want to do a full rebuild, it really pays to have it all done by someone who does it all the time. You probably need to go through it all at that point.
Replating the cylinder, all new bearrings, several seals, and a expert's eye can get you several years of reliable riding time.
Ok, I'm rambling on, Black smoke would be excess fuel. It would probably be barely running if itwas doing that.
White smoke would be water, which is way bad. Head gasket, or something worse like broken water jackets.
Blue Smoke, funky smellin blue smoke, could mean oil seals.
Winter is coming up, keep an eye on it, and be prepared if it needs it.