I look at it like this: a crash pad will be 200-300 bucks, and not reimbursable (which is dumb, but I digress...), so if you spend it, you're out of pocket that amount, regardless.

Hotel rooms are 60-70 a night, reimbursable up to $250. If you spend over that $250, but less than that amount plus whatever a crashpad would cost, you still come out ahead. Basically you'd have to be spending more than $500-ish each month in hotel rooms for a crash pad to make financial sense.

As for getting stuck with commuting to reserve, bid for the late period, and every time you talk to scheduling just tell them you'll do whatever they need, so long as they don't make you spend the night in base. You'll be doing whatever they ask anyway, but you might as well try and get something for it.