I definitely have to stop more in the winter time on road trips, but that's just the nature of how EVs work. On the upside Tesla puts superchargers in spots that make it easy to take a break for a rest stop anyway.
I do miss how quick gas station stops are with ICE cars when doing a road trip, especially if you're on a constrained schedule, but the benefits of having the EV have outweighed it so far, especially with most of my daily miles being in the city (where the EV really shines).