I've got a 55' Mercury Monterey. Its in decent shape. I replaced the carb, water pump, alt, interior ( sort of) shocks, brakes, tires, wires, ignition system, and so on. I've owned it for 7 years now. Up until probably 4 years ago, I drove it to work about 1-2 times a week. But since then I've gotten jobs that are always at least 40-50 miles each way. I'm not comfortable driving it that far since it has no power steering or power brakes and it wears me out driving it that far ( its a HUGE car) and also because its old and full of worn suspension components. So for the most part it sits covered up in the street. It might get driven about once every two weeks around town. I start the engine every week and let it warm up to keep everything in good shape.
But for a few years I've kicked around the idea of selling it and getting something " newer", like maybe a late 70's Vette or maybe even a early to mid 60's Datsun or some other car that could actually be driven to work more often. The Mercury isn't worth a whole lot being a 4 door and all. It might bring $4,500-$5,000.
On the other hand the Mercury runs great and has no problems. Plus I know it inside and out. I don't have tons and tons of time to repair another old car. We don't plan to have the same living situation like we do now forever, thus things will change.
What would some of you all do?