I've been having similar thoughts about my Celica.

On one hand, I love the damn thing in all its PITA glory. On the other hand, I own a home and could really use a truck/something with a tow package. The wife has an SUV (Enclave) without a tow package and I regretted that since we bought it. I can't afford to pick up a beater truck as I just dumped a bunch of money to landscape our backyard (all of that in the back was terribly sloped, so I had a rockery installed and had it re-graded).

I've always wanted a Wrangler, but there's a nice 4Runner for sale/trade nearby that's pretty enticing. Then, there's a Miata that's trying to garner my interest. Ugh.