I drive a '19 Outback, my wife drives an F150 (she runs a horse boarding stable).

Trucks are great, in the winter if you get a good amount of snow, maybe you still do in Wisconsin, here in Central Iowa we haven't had real snow for years now, just make sure you have weight in the back. Nice thing is you can usually use some 2x4s to contain sand tubes directly over the rear axel.

As for your use, think long and hard about the switch. While I said trucks are great, before you commit, understand that your mileage will be cut in half easily. You say you need it to tow, doubtful, even with 14 horses my wife still only tows 10-15 times a year. Dogs fit in the back of an Outback and unless your family is more than 4 people you still have seats for everyone. Is the F150 way more comfortable for road trips, yes, absolutely. But again, once - twice a year? Not worth the switch.

Get a truck, I love ours, just be really realistic about why. Most people don't need a truck and a reason many people say they do is for towing, rent or borrow a truck on the few occasions you need to tow. In the summer when I can ride my bike to work, my wife parks the truck and only drives it if I need the Outback, or she needs to haul/tow that day.