I would Google "
trip insurance" and check with some of the insurance companies.
I don't really think the points basis of
DVC rentals should be an impediment to you getting trip insurance. Obviously it is if you are buying
DVC's trip insurance, but not if you are purchasing your own.
I wouldn't even mention the concept of points. You are dealing with a private individual and you are renting X# of nights' accommodations from them for X$, just like you rented a ski condo from someone. How I get accommodations to rent to you - and what/how I pay for them - is irrelevent, as long as the insurance company is okay with the private rental
I would explain the private rental nature of the deal to the insurance carrier up front and be sure that is an acceptable type of rental for them to cover. It may or may not be.
[Incidentally, if you find a company that will write trip insurance for private rentals, that would be very good information to post here. It would be helpful to a lot of people -- both owners and those renting points from us.]
I would also make sure the DVC owner renting the points knew that you were buying trip insurance, and that they would be prepared to furnish you with a "Paid in Full" invoice for the rental in the event you needed it for insurance purposes.