Looked at a 1993 DR250Se. It ran good, for the year, was in better than average condition, not mint. When I rode it and shifted from 5th to 6th, it would go into a Neutral. I thought it just might be me, but not so sure about that.

So, does anyone know if there are inherent issues like this with the DRs? What would cause a me to hit a Neutral between those gears?

It missed the gear or dropped out of the gear once you selected it? It could be the shift forks for that gear... Or the gear itself being worn and not retaining their position or whatever...

if you're hooked on the bike then it might mean a case cracking to fix the problem... Otherwise I'd recommend moving on to another bike... Transmissions don't normally just drop out of gears unless there's something worn or broken or bent or not right..

I'm not a bike mechanic, didn't stay in a holiday inn express, and usually don't know what I'm talking about.

Its not popping out of gear per se. When I shift from 5th to 6th, its not catching the gear and going into a "neutral" free revving position. The way Ive always known bikes, if you dont get the shift right it would just stay in the gear you started out in. Meaning if I didnt get 6th gear engaged properly it should just stay in 5th, not go "in-between" gears and go into a neutral.

Sounds like it might be a bent shift fork or the shift drum might also be messed up. Was probably tipped or crashed on the shifter which took the force and transferred it to either the fork bending it, or the shift drum and messing up the channels the fork rides in.

If you're confident enough to try fixing it yourself, it shouldn't be that expensive, worst part will be splitting the case and not mixing up or losing any tranny parts.

ETA- I would pass on the bike if you don't have the experience or confidence to fix it yourself.