The only major unexpected problems I've encountered (and I probably should have expected it) have had to do with family members asking for money to help them with various things. I'm talking mostly about kids here (my two stepkids), but my two siblings also ask for money from time to time. These are all people that are terrible at managing their own money (one has a good job, the others earn very little), and they all know that my wife and I have some resources (as we have been frugal and manage our finances well). These requests all start out as "loan" requests (the car broke down, I need a security deposit for a new apartment, etc, etc), but you know how that goes.......it's obvious that most of the money is never going to be repaid, especially from the stepkids. And sure, we could just say NO to all these requests, but there are extenuating circumstances that make that difficult (like the two grandsons the stepdaughter has, that need a place to live, and a car that works, etc). I don't know if others on the forum have this problem, but we sure do, and there is no apparent end to it. This just bugs me because all the financial planning I do for the future basically has a "margin of error" due to things like this, which are (largely) out of my control.