How do you know when to sell?

[Dave Rifkin]

How do you guys decide when to sell your cars? I know many of you sell in order to make room for another purchase.

Unfortunately I am not in that boat; if I sell my car I will not be replacing it with anything which is why I am struggling with the notion of selling it. The car in question is my 1969 L46 Corvette coupe.
I have had it for close to 10 years now and have done little things such as redid the interior, bought new rims / tires and was fortunate enough to have Eric rebuild the Quadrajet and Albert got it running right with the help of his friend Joe.

The issue I am having is I don't drive it enough. I almost feel bad for having it as it sits in the garage 90% of the time. I have a 2002 Z06 that gets driven more than the '69 mainly because it's more comfortable, faster, gets better gas mileage; etc.

The '69 is paid for and isn't costing me a dime to keep aside from insurance. I don't have the money, time or expertise to do most of the things I would like to do to it which leaves me paying people to perform these jobs for me. $$$$

Since C3's don't seem to be appreciating at a rapid pace I am not concerned about selling something that, one day, could be worth a ton of money.

So, do any of you ever have these types of struggles and, if so, how do you deal with them?