No extended trips yet, but from the long tours I've seen, they either have very flexible jobs or they just quit and worry about it afterwards. I try to organize my trips around holiday weeks, that way I use less vaca days to do a week trip.
I am debt free, so when I know a trip is coming up, I set aside some funds for several months, which just means not going out to eat and such.
Most trips have been solo, so no comment on company.