I am a
DVC owner with only a small contract. I love renting!!!!! I have done it about 5 - 6 times.
SUPER CON .. are no cancelling (often) and you gotta trust them.
If you book 11 months out and something happens.. you are stuck, alot of rental companies will not even try and get you a different resort/time ect.
I will rent if it is a last minute trip, or have back up plans and will not book with a landlord until about 60 days out. I think renting is the best/cheapest way with little risk there is. IF YOU TRUST THEM! I will not rent more than 3 months out. People sometimes rent there points, due to lack of $$, and MS will cancel ressie without payments; and though possible in 3 months, way more likely 9 - 10 - 11 months out that it would happen.
I often book a resort with Disney; (Like I am aiming to book BB promo hoping for FD at the Poly in Aug when I go). At about 60 days out I will try renting points for BLT, BC, BW, or SSR and it will be around 8$ - 9$ or so with a short time left. If it doesn't work out.. i have a back up! I have until 45 days to cancel with no cost to me with my Disney RSVP. (AND I will take it if I cannot get in at a DVC I want.) Win win for me. I have done this about 4 times with success. I have booked AP room only at FQ and cancelled it 5 or 6 days in advance to rent someones points for 6-8$ a point.
Con, (for me it is okay) in this instance.. is you have to be okay with SSR, and with switching last minute. For me.. renting a 1 bedroom at SSR for less than 700$ for 5 nights, is an easy choice over the Poly for 2,400$ for same time.