The Short: Current car (2002 PT Cruiser) needs to be replaced quickly. Would you buy a used manual 2009 Subaru Outback and learn to drive a manual? Or would you buy a used 2007 Jeep Grand Cherokee (automatic) and wait for another Outback in a year or two?

The Long: My current car is a 2002 PT Cruiser. It's on its last leg. The A/C has been out since May and it would cost approximately $600 to replace the part not including man hours. It's not practical to replace it because the back hatch doesn't have a large enough capacity for things like trips to the campground and the back seat cannot safely fit two convertible car seats. It's a struggle with just one and an infant car seat.

This weekend we found online in a dealership in KY a 2009 Subura Outback. It's exactly what we're looking for in the price range and everything, plus it's a nice color, good interior, etc. The only thing that isn't good about it? It's a manual. I've never driven a manual. DH does. The thing is this is supposed to be my car. I would have to learn how to drive it. It could be months before I'm comfortable driving it by myself, especially with two small children in the car.

My parents offered up another solution. They're willing to sell us their 2007 Jeep Grand Cherokee, which I've driven before because it's an automatic. I would be able to fit in the car seats but don't know about our double stroller and etc for trips. Plus DH isn't thrilled with the feel of the transmission (thinks it feels like a rubber band. He's also concerned about the kids at some point wanting to climb up in on their own and it being so high off the ground. He doesn't think it would be safer. In other words, he's really against it.

But I wouldn't have to learn to drive it. I've driven it before. I'm comfortable with it. I would be able to drive it without him helping me. Which means I'd be able to get the kids out more. Story time at the library. Trips to the park. And all without having to wait for DH. But... I don't really like driving. It's not my thing. DH likes taking long drives, I like just going along for the ride. Which means even if I could get out more because I could drive the car, he'd still need to feel comfortable with it because he drives the family more.

But but but - there are so many buts that go in so many directions. If we get the Jeep and try to sell it in a few years, that seems ridiculous. Why try to finance a car if you aren't going to pay it all off? Like why buy a starter house (in our situation, with two kids) when we'd need to upgrade in such a short time frame. It seems most logical to go with the Subaru, learn to drive a manual, because it's a better car for the family. Better stylistically, size wise, etc. but the Jeep has no learning curve...

You can see why this is a merry go round...

And just for fun, pretend the cost is similar and not a factor - because it practically is.