Exactly why I love renting DVC pts! We started staying with DVC pts a few years ago and I dont' wanna go back, lol! We could never stay deluxe without going this route! It's great staying deluxe while paying prices for a studio that are less than a mod, usually even with a sale. We paid about $1260 for AKL studio a couple years ago, would have been over $3000 for our Dec trip, even with a sale. This past year we did BCV studio for $1400 instead of close to $4000 for our Dec trip. We've got a trip booked to BWV this year in Dec, and again very happy with everything!
We've had a great experience everytime so far, and no trouble at all. The only real drawback I see is the not being able to cancel. The owners, I found all here on the Dis, have always set up ME or dining plan when needed. We did food OOP this past year and it was great so doing that again this year. One year we were able to were able to set up our own ME, but this past year they wouldn't even talk to me, so the owner set it up for me. Easily accessed my resort ressies to link to MDE for FP+ and ADR's. Been getting tickets through UCT for several years now, and converted the last ones we got into AP's to cover this coming trip in Dec.
I think to be able to have your best shot of booking the resort you really want, it's best to try to find someone by the 11 month mark! But, if I was gonna book a trip on less notice, I'd still try to find something thru renting DVC pts for sure, just might have less choice in getting the exact resort I might want, but there are lots of choices.
I guess insurance would probably be a good thing, though I've never done it, mainly because I wasn't sure where to look or what would be good prices. But it could certainly give more peace of mind if one was worried about possibly having to cancel. Also, you can always have a contract with the owner of the pts so you can feel more comfortable with the rental.
I definitely recommend renting DVC pts and plan to continue doing so myself whenever I possibly can!