The other thing to keep in mind is that "headwinds into rising
terrain" is dangerous simply from a mountain flying perspective,
simply because (at least at TRK), your basically flying straight
towards the rotors coming off the Donner Pass, and their associated
turbulence and smash-plane-into-ground downdrafts. As I'm sure you
know, flying perpendicularly towards a mountain ridge without
sufficiant (several thousand) feet of clearance is ALWAYS a bad idea,
especially after take-off and even more so if your also flying into a
head-wind. 45 Degree approach, always - give yourself that out.

Crosswind takeoffs are a no brainer, the only risk is traffic, and
that's what CTAF is for. So yeah, I would have to agree your better
off going crosswind and taking your time to build energy.