My sense of adventure has admittedly dwindled. I had an 89 245 in very rough shape, that I drove EVERYWHERE starting immediately after buying it and throwing an O2 sensor in it. Within a month I drove it from the southern tip of IL to the twin cities in MN and back in one weekend without any tools or spare parts. It was an amazing time with close friends and no break downs. About a month after that I took a very daring trip alone from Southern Illinois to Lansing MI which was completely uncharted territory for me. Again, no breakdowns and I enjoyed myself.
Fast forward about seven years. My trusty 240 is long scrapped after a failed restoration, but my girlfriend has a very similar '89 245 in seemingly great condition. It came with very detailed documentation and service records, and we drove it home to Indy from Milwaukee on a sketchy at best timing belt. It's been a pain in my rear ever since. Spontaneous water and vacuum leaks made it hard to trust for a while. Then as of yesterday, we lost rear braking power. I guess you win some and you lose some.
It's funny how as I gain more knowledge and comfort on fixing cars I also lose my trust in old cars as daily drivers. It's easy to stay on top of the repairs and maintenance of old cars when you don't depend on them, but when you drive them all the time it's easy to fall behind and sometimes seemingly impossible to catch up. However, we still love the car to death, and a 245 wasn't meant to be a weekend warrior. If it ever has a major failure, I'll probably buy it, swap in a more modern fuel efficient drive train, and drive it until the wheels fall off again. I'll still keep my newer cars with creature comforts on the long-distance road trip duties though.