I must admit....even as a novice traveler, my medications were always in my purse - with extras in my check-in luggage. Although I read all the time that people have put their meds in their check-in luggage, I still have a hard time understanding why they would do that...
As far as their finances, we have no idea why they were on such a strict budget. Perhaps they had a better budget when the vacation was planned, but they had an unexpected expense come up before the trip. I really don't think we can judge them on this without knowing their whole financial history.