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I was wondering whether most people incur significant ($100 and above) out-of-pocket expenses for ASW, after receiving travel stipends/reimbursement.

I stupidly let go of a great deal from SF to Duke last week that would have allowed me to work all day Thursday and still make it to the Friday Open House on time. Now, the cheapest flights that are eligible for reimbursement require me to spend $200 above the travel stipend AND miss work on thursday. I also have no vacation time left so would have to either take unpaid leave for 2 days now or come up with some sob story about deathly illness...

now debating whether i should miss the ASW...

Depends on the school and what the ASW schedule entails (school might have a schedule up on the website?), but you'll probably be on your own for at least a few meals. Plus transportation between airport/lodging/school.