To be sure nothing freezes, I winterize when there is any possibilty of temperatures going below freezing, detwinterize and use plumbing only when using in temperatures above freezing. Can't help with the taking it skiing issue, my winter runs are in the direction of someplace warmer.
Take out anything that might freeze and burst. I take out all edibles for storage, all liquids for cold storage, don't want to welcome critters in for a feed.
Batteries need periodic charging, also helps drive train and tires to run highway speeds 30 minutes to a couple hours every month or two. Mine is out of storage, in the driveway for battery charging right now, because it got warm enpugh to do so, and had not been out since end of October. Took it for a 50 mile ride ride to warm it up, warm up and flex the tires, redistribute plasticizers that leach from tires at the rubber surface.
If you want to store freezing, you need to winterize. If you want to use plumbing, you have to dewinterize. It is only as much of a hassle as you want to make it. For some rigs and storage conditions, draining is enough. Blowing out lines with air would be more work, some people find that is more work than putting in antifreeze, but it is less work to dewinterize if you don't use antifreeze. I've tried blowing out lines on mine, it is about 3x the work of pumping in antifreeze and the experience left me no confidance that the lines were dry where they needed to be dry.
If you can't do this yourself, it definitely will be a hassle, trying to schedule dealer service for the job at each end of every trip. What you can do yourself, what maintenance you require someone to do for you, will be a big factor for how usable any type of RV is for winter trips every 1-2 weeks.
All my experience is dewinterizing, rewinterizing, in temperatures above freezing. I suspect either process is trickier with temperatures 10, 20, 40 F below freezing. Think about that, with respect to what you want to do. With most Cs or many TTs, there will be temperatures below which plumbing is not usable, even with heat on. There are motorcoaches that are used continuously in very cold weather, but they are designed for it, all plumbing in heated spaces, and those spaces heated all the time the coach is out of the garage.
I check tire pressures every time the RV starts a trip. I check tires, engine fluid levels at the start of every driving day. Really, should do that for the car too, rather than just at the start of trips.