What about it is more difficult? The (admittedly few) off-sites I've been to have been scheduled 6+ months in advance and the general expectation is that everyo

What about it is more difficult? The (admittedly few) off-sites I've been to have been scheduled 6+ months in advance and the general expectation is that everyone is going unless there's a wedding or a kid is sick or something, in the sense that it's not really culturally acceptable to take PTO during that time unless it's for something very important. When the VP or CTO comes around in February and says "we're going to $CITY for a week, all expenses paid, in September" it's pretty easy for all the teams to get around that.