Top down, chrome spinning?

This weekend was one of the first really nice weekends of the year. I was driving to the gym on Saturday in my truck, windows down, backpack rap blasting on the stereo, and thinking, man, it would be awesome to have a convertible.

And then I started thinking - maybe I should buy one.

I've been toying with the idea of buying a second car for a while- something fun, for occasional driving.

My thought is that I could buy an '83-89 Chrysler LeBaron Convertible cheap - I've seen running ones go on eBay for <$2000. I picked that year range because if it's 20 model years or older, it's considered old enough to get Historic plates in the state of Maryland, which drops registration fees by about 75%, plus means I don't need to get it smogged.

I'm thinking it wouldn't add much to my insurance, and parts would be cheap, since it's the same components as pretty much every Chrysler made in the 80's and 90's.

My first car was a LeBaron - a hand me down sedan, complete with vinyl roof. It was dorky, but it beat taking the yellow bus or getting a ride from mommy. It's not the, umm, most exciting car, but most of the other convertibles from the 80's are harder to find because so few were sold (Infiniti M30, Mazda RX-7, Toyota Celica), cost more (because they are made from more desirable cars like Camaros or Mustangs) or are expensive to fix (Mercedes, Saab).

But it mostly comes down to if I can pry open my wallet. I'm generally resistant to spending money on anything fun. There is absolutely no financial justification for this - it's spending money on something I hope will be enjoyable, but it's going to cost me money. Part of me thinks I should let myself spend money on things that I enjoy - that I deserve to treat myself for my hard work. But for the most part, I try to live frugally - I eat cheap, I try to pick up extra overtime and extra cash from reselling stuff, I don't buy expensive electronics or travel or much else beyond the necessities. I feel like, even though my job is fairly secure, that I should try to stockpile as much cash as humanly possible just in case. But at some point I need to start doing things I enjoy, and that means spending money.

But I'd be surprised if I can convince myself to actually go through with this. Which may be because it's a bad idea, but also because I think I'm completely incapable of spending money if I don't have to.