Originally Posted by
slivrflyr
//edit. Or would it be better to find third party insurance and prepay for a year of coverage for trips up to X days.
This is what I do. Or more accurately, I buy per-trip 3rd party insurance for the one or two big trips/vacations where I want to be able to quickly recover from IRROPs, lost luggage, etc. and move on with my trip without having to think about it.
For small domestic trips I basically just "self insure", and for work trips I'll get reimbursed for critical needs (maybe not for replacing clothes, but if that ever happens I assume I'll get to keep the clothes for personal use afterward so I don't necessarily mind having to buy them).