I have a '98 CR250 that is a pain to start, but once it gets warmed up its easy to start after that. Its just starting it up when it is cold most of the time me and my buddy take turns kicking it until it starts. Any suggestions would help.
It's probably the reeds. Worn, warped, chipped or cracked reeds will cause this. I had a freshly rebuilt '99 CR motor that was near impossible to cold start. Started great when warm. Changed the reeds and it was a first kick starter.
Also, if the top end is totally worn out (needs new rings at least and maybe a piston) a two stroke can be very difficult to cold start. If you know the top end is in good shape, it is very likely to be the reeds.
I hate kicking on a cold engine. On all my CRs I lay the bike on its side to get fuel in it and if it doesn't after two kicks repeat. Works for me, and doesn't cost anything. Might try it.
Yep - I lay mine down for a good 5 or 10 seconds on the left side until gas is really running strong out the overflow. Pick it up, prime it by kicking through slowly a few times, find top dead center (kick slowly against the compression stroke and just as it gets easier you are at TDC). Then give just a tiny tiny bit of throttle and kick it hard. Did not work when my reeds wore out, though.
I do the same with my 98 cr250 as the guys above, lean it over and let some gas spill out, get the piston to tdc and give her a hard kick. Mine fires up everytime after that.