How do you know when to sell?
 

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?

For me, I just knew it was time. Had my 69 Chevelle SS 396 since 1980. Lots of memories, but the pure enjoyment of driving it everywhere was replaced with fear of damaging it.

Still have the awesome memories, but I have no regrets. Probably because i have another old car I enjoy driving frequently. Working AC is a bonus.