I don't want to Start a massive debate on payback but for me when I hear people say I reached payback really quickly I'm still unsure how to evaluate that
I don't compare my DVC outlay to the cost of staying in deluxe hotel rooms or DVC villas for cash as I might have wanted to do that but I would never have paid out the cash to do that.
That's a correct point, but...
My first visit to Disneyland resort I couldn't use my DVC because I had just closed the contract and it was a trip with short notice, so I booked a cheap motel on Harbour boulevard for $77 a night. I'm heading to Disneyland again this November and I'm staying on points at the Grand Californian. I'm paying $300 in MF alone for the points used for the reservation, so I'm actually paying more with DVC, even not considering the buy in cost.
However a comparable stay would have been $1700 at rack rates: no way I would ever pay that for three nights! DVC allows me to stay in the flagship resort and enjoy my stay much more than I would without it. What's the value of this? Has happyness a price? That's why I think that using rack rates for comparison and deciding when you break even has still some sense. It measures the added value you get from DVC, even if you would not book that room using cash.
We love the relaxed vibe of old key west and also love the space and facilities of 1 bed villas so would probably aim for there as our home resort. In fact we've never stayed in 1 room with our 2 kids at Disney so we've been really spoilt by OKW! When the kids were little we used to stay off site so are used to space and self catering.
Getting OKW at 7 months during the summer season it's not difficult. DVC busier season is from late September to Marathon week end in January. Other periods are much easier to get and Summer surprisingly is not difficult to book at all. Some resorts would be difficult/impossible to get (BCV, standard rooms at BWV and BLT, VGF and value rooms at AKV), but at OKW it shouldn't be a problem, unless you want the Hospitality House category. That's to say that maybe SSR could be a good purchase too. It has lower MFs and on the long run it'll be a huge saving.
OKW also has two espiration dates, 2042 can be cheaper but Disney often ROFRs these contracts to resell them with longer expiration date. 2057 are more difficult to find (while SSR already has a longer expiration date).
1 bed villas are the easiest category to book too.
Many say: "Buy where you want to stay". It's good advice if you are really sold on one resort, you would stay there most of the time and you'd be disappointed if you cannot stay there. However if you think you'll use your points at different resorts over time, then paying more doesn't make much sense. I'm with who says: "buy the cheapest resort where you wouldn't mind staying". For me it was SSR.