Typhoon
That is always a tough call. We had an old Lumina mini-van that I thought was awesome. Thing seated 7 comfortably and with seat removal offered a lot of space to haul large items. It needed over 1k in AC repair, and in Texas it's tough driving it without AC. I suffered through most of the summer, and had some maintenance done on it. Found out that this minivan had what I recall was over 200k on it, had NEVER had the transmission fluid changed.
At that point, I feared many things were going to start breaking down including the tranny. I could handle driving it in the 100+ temps but thought the thing was going to become a money pit. The worst part of that is the time involved. If you rely on that vehicle and it's out of commission for any length of time it creates a lot of issues. I could've waited to see what happened next but decided to bail.
The vehicle I replaced it with in 2008 is still going strong with barely over 100k on it and has never been in the shop for anything but tires, state inspections and oil changes. I think I made a wise choice to move on when I did, but one never knows, for sure, where the line is. I guess it's different for everyone.