Let me preface this discussion by saying that I bought a '97 Dodge Dakota 318 earlier this year and I commute 40 miles for work every day. At 15mpg, it's killing me. I'm racked with guilt every day driving the Dakota; I'm the only person in it and 95% of the time I don't need the size or power that it has. With the increased gas consumption, higher insurance and car payments, it's really putting a damper on our finances. I have to have a tow rig for the boat and I refuse to put a hitch on the wife's SUV. We're also going to be having kid(s) soon (I hope) and I need something I can put baby seats in for those times when I'll be hauling the kid(s) somewhere.
So there's a Jeep Commando sitting around the corner from my house. I look at it every time I drive that way. Here's an example of what it looks like:

I like the idea that it's a hard top convertible. I have it in my head that I want some kind of convertible in my life and whatever convertible I got I would keep for the rest of my life. On the other hand, it's sitting on two flat tires, is pretty well thrashed from one end to the other and hasn't been registered since 2000. Overall, it's not bad but there's some rust here and there, seals that would have to be replaced and the interior is a shambles. I have no idea what's wrong with it nor do I have a garage to put it in so I can work on it. From a driveline perspective, the engine and transmission are easily replaceable with newer, more standard plants. The body and interior are fluff and can be upgraded as needed after the mechanical stuff is taken care of. I'm no stranger to car repair and have friends that could help with dropping in a new engine and tranny if needed.
The idea is that I sell the gas hog truck, get a sport sedan that gets more respectable gas mileage and get the Jeep for towing. After all, most of my driving is to and from work. Fishing trips only happen on the weekends and vacation days anyway.
So here I sit. The drifter restoration isn't even complete yet. I have all sorts of projects around the house to deal with. And I'm thinking of taking on a project car. Am I insane? Am I just a glutton for punishment? Is this a massively bad idea? Or should I go for it? I haven't asked about buying it and they may not even want to sell it. I wouldn't pay more than $1k for it if I could buy it.