Totally possible.
Each set of wheels with their own TPMS. I put aftermarket sensors in my winters... there's one brand out there known to be compatible. Bought those.
(Now Tesla TPMS have gotten cheaper for spares... so you might just get them from Tesla).
(Or, run without TPMS for the season that you care to take the most chances. Working TPMS's are not critical for driving dynamics.)
Each time you swap, you hit the calibrate button. Drive a bit, and you're done.
FYI the TPMS's have a battery lifetime... before they must be swapped out. My tire guy says, the wheels that aren't spinning don't use their battery power to transmit.
Extends battery life of the TPMS's makes sense..
Plus it means you can carry an extra set of fully loaded wheels in the car on the way to the tire shop to swap them onto the car, and not confuse the TPMS monitor along the way.