The biggest chunk of "winterizing" is getting the water lines purged of water and filled with anti-freeze. Regardless of the type of RV, frozen water lines is something to be avoided. So, if you take the RV out in the winter and put water in the plumbing, you will need to "winterize" again before things freeze. After you "winterize" a few times, you'll find it doesn't take all that long to do.
Your diesel will survive outdoors between outings. I would suggest that you keep all the batteries fully charged which most likely means at the least an extension cord to the RV to keep the battery charger or chargers operating. (Be sure both house and chassis batteries are getting charged.)
The bigger inconvenience will be when you want to leave and the RV is snowed in.... More and more places it is illegal to drive with snow accumulation on the roof, and the more goodies are installed on the roof, the harder it is to clear off without damaging something.
Don & Anita Sweger
98 Overland Larado 4141SO
41' 325hp Cummins C8.3 Nicknamed "Lola"
Owners of: www.tvformyrv.com