I recently spoke with a woman who was beleaguered by the fact that she was tasked with selling the remains of her dead brother's estate, a depressing task under normal circumstances. However, she faced the additional burden of realizing her sibling had acquired a lot of crap and left this planet with bills to pay. '
It gave me pause because you could see any sadness for her brother's death had been replaced by annoyance, and perhaps even a dose of shame. Not only was he destitute, but he had horrible taste and instincts when it came to what to spend his limited funds on. Would my loved ones ever have a similar reaction when it came to unloading what remained in the garage when I kicked the bucket?
Candidly, I don't think so. This is a strange lens to view your car hobby through, but it's important to consider, especially if you're inclined to holding rather than selling. Is what you're buying at least somewhat rare? Great, but rare doesn't mean desirable. Is it rare and a hoot to drive? That's a safe bet. A "hoot" doesn't mean fast, mind you - it could be painfully slow but charming; average performance but a crowd-pleaser at Cars & Coffee. Just don't buy something that fails at all of those sensory experiences.
While I do think some generations like the brass era and 1960s muscle cars will go through a painful correction depending on when you bought, maintained examples with great documentation (remember, you can use The Common Gear to store all of your records in a digital portfolio) will remain popular until the last guy capable of repairing an REO or an Avanti has passed away.
Personally, I am grappling with the fact I bought and lightly restored two motorcycles I have zero hope of riding in the next few months. The 1993 Honda VFR750F was briefly considered as a sellable asset until I did some reading and remembered what a special bike it is, not only for that wicked V4 noise but also because the Pearl White examples with matching white wheels are one-year-only models. Could I put an easy $5K in my pocket? Sure. Do I need it that badly? Well, yes and no; there's a new project that will eat up some resources, but at the end of the day, I'd rather have the bike remain in my possession until the rational argument for keeping it becomes indefensible.
It's OK to leave some things behind, but do so with an eye towards whether the effort to market and sell it without your direct involvement will be worth the time for your heirs - and remember, if you store all vehicle documentation and records here on The Common Gear, it will be far easier to find a new owner whether you're among the living or not.