Oh one more thing that's scaring me a bit is the whole chair lift thing! I've read so many horror stories about getting on and off these with a board... is it really that hard to do?
Depends on the chairlift. Getting on is easy, getting off can be combersome with some, e.g. if they have a little downward slope and bend right after getting off.
Newer ones have transmission at the stations thus they are slower at the stations and you have plenty time to get on/off. Older ones without transmission can be a bit of a hassle to get off, you need to skate away from the chair faster. Try to get the outer most seat the first time when you don't know yet how the upper station lookks like, so you can get out of the way and are not sqeezed inbetween ppl left and right. And do exercise skating. You're calmer if you know that you can tackle some meters downward without being strapped in with the hind leg.
T-bars are easier to get off but more challenging to stay on