Have i Lost It? ( Long Rant)
Snow? Creature comforts? Heck my defroster doesn't even work right, stupid vacuum controlled heater doors...
So, here's an exercise for you. How much will you need to spend on this third vehicle? A few thousand dollars? Now also consider that you'll have to pay insurance and registration for the extra car, as well as upkeep (oil changes, tires, etc).
Now, if you took that money and put it into your Swinger, I'm guessing you could probably cure a lot of what bugs you. A complete Vintage Air system fitted to your car would solve AC and heat problems, heated seats and mirrors can probably be adapted out of a late model. Wiring harness with more accessory connections? New door seals? Haven't even scratched the surface of what a "cheap" third car would set you back, let alone ongoing costs like insurance and registration.
I drive my Challenger in the snow. Even on unpaved, unplowed roads. Unlike what you may hear from others, unless they salt the roads heavily these cars don't melt. I've heard rumors that these Mopars were actually intended to be driven outside! You know, when the weather isn't sunny and between 60-85*F...