So for my serious response...
We talked about this when you were down - if you don't have any roads on which to enjoy the Cayman, I'd sell it. I contemplate this from time to time with the Boxster, but then I get to drive it on a fun road taking the long way to get somewhere and it seems irreplaceable. Your call on that one.
If I were you, I'd sell the wagon. I understand the desire to have something like that as a winter beater, but it's going to be too maintenance-intensive to keep long term as an occasional use vehicle. But, y'know, you own it... can you put a hitch on it and tow a utility trailer? If said hitch bolted in, all the better, because it's going to be ... uh ... challenging to weld to the wagon.
As far as trucks go, the Tacoma sucks. It doesn't ride well, the seats are uncomfortable, and they get pretty miserable mileage. They are also really expensive, but having said that, people love them so it will hold its value really well, so if you do ever sell it it's probably the most economical choice. Did Toyota ever fix the problem with their frames rusting out? One of my coworkers had to have his frame replaced (yes, they replaced it) on a relatively low-mileage truck.
I haven't driven a Colorado, but it's supposed to be really good. It's also a GM, and that brings with it everything you think it does.
The Ridgeline isn't a truck. It's more like a modern el Camino. It lacks the shortcomings of most trucks, but it also falls short on the utility of most trucks. People who hate trucks love them. People who love trucks hate them.
I despise Subarus, but it seems like what you want is a Subaru with a trailer hitch.
