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What I've always heard about stubborn transmissions is that a shift fork could be bent, or the shift drum is damaged. Not necessarily the case with you, but it's what I've read in other cases where shifting has become a problem. I'm just not sure, short of severe abuse, or dropping, how these items could be damaged.
The only thing you can really do externally to improve the situation is to adjust the shift lever downward a little to a position where you have more lifting power. If a shift lever is adjusted too far upward, I have trouble shifting and often miss a shift completely.
The other thing you can do change to a different oil. I've tried a lot of different oils in the bikes I've had, and found that Valvoline made my '94 250 impossible to shift, and Mobil1 caused my brand new clutch to behave more like an On/Off switch. My current 250 seems to like Rotella T6.
If this is a constant problem, I'd suggest you have the mechanism looked at. I missed a 4-5 shift for no apparent reason the other night, but so far that has proven to be an isolated incident. If it happened more often than not, that would be an indicator of a mechanical issue.
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