Have you considered renting points from a DVC member? We did this on our last two vacations and couldn't have been happier. In fact, my wife and I are currently moving forward with a DVC investment of our own.
On our last two stays, we stayed at a 2-bedroom at Old Key West. Party included DW, toddler son and my parents. Cost of the room was split 50/50 with my parents.
Having traveled during the off-season, the DVC point cost for our 2B at OKW was 22 pts per day, Sunday to Thursday. Points commonly rent for $10 each from current DVC members--some charge a little more, some a little less.
So the effective room rate was $220 per night, which included all taxes and fees. Since we split the cost, my parents and I each paid $110 per night. You'd be lucky to get a moderate for that cost once you factor in the room taxes. Payment was made entirely to the DVC member. We paid nothing at the resort itself.
Rack rate for this room was $479 plus tax per night.
OKW is a fabulous resort. The 2B provided us with sleeping accommodations for up to 8, a full balcony (with LBV golf course view), a full kitchen and living room to share, in-room laundry facilities, etc. We also received the full DVC member treatment throughout our stay--including any applicable DVC member discounts on merchandise and dining.
The point "cost" of a room does increase dramatically on a Friday/Saturday, but you don't appear to be opposed to a little resort hopping. If you go this route, I'd merely suggest hopping to another resort and paying cash.
For more info, check out the dedicated DVC boards here. Or you're welcome to PM me for a couple of references. Both point renters I worked through were very helpful and professional throughout the process.
