This happened on my 1st day of the challenge (M2 match from AA PPro so trying to get to 50 tiles anyway). I had a BOS-ORD-BOS to start the day which was fine because most of these out and backs use the same plane, and at worst, I'd have to connect through JFK on the way back. Later that day, I also had a BOS-LAX nonstop ($134 with AA miles on the way back) that I switched to BOS-BUF-LAX, but the BOS-BUF flight got delayed 4 hours, so I just canceled that itinerary. Probably for the best because that would've been 18 hours of flying. I only have 2 trips with 2 or more destinations at this point. If I were untethered (just my job) with 20 years younger me, I am certain I could do this challenge for under $2.3k all in (T pass plus book Basic on the way back from out and backs but I like EMS too much). As it stands, I have the whole challenge booked, and I'm looking at around $3,900 (with maybe 20k AA miles for positioning) including occasional parking at Logan economy when getting a ride doesn't work - also zero need for hotel stays (just canceled an ORH-RSW-ORH that required an overnight that I just don't want to do). I'm really taking advantage of lounge food and drink, though.

Also happened on my 2nd day - ACK fog delay in the middle of BOS-ACK-LGA, but I knew in booking it that it (almost?) always used the same plane. "Lady on the Plane" said, "you're doing the 25, too?" when I reboarded. Guess I'm not the only nutjob.