As I said, we're not picky about room size. We don't spend enough time in the room to really care. Not sure what room you're looking at for that kind of money at the WL, but we're staying for 10 nights at the Polynesian for $4,000 (and probably much less when the AP discounts come out.)
According to allears.net, a one bedroom villa at Wilderness Lodge for that time period in July THIS year is $530 a night. Once you include the state sales tax and the county resort tax, you're a hair shy of $6000 for a 10-night stay. LuvtheGoof's numbers are pretty much spot on. Go to
http://allears.net/acc/faq_wlv.htm and look for the pricing chart. Granted, these are "rack rates" and do not take any sort of promotion into consideration.
On the one hand, you're right that when Disney hypes a "break even" point to potential DVC members, they're usually comparing rack rates and not factoring promotional prices. But you also have to admit a: there's no 100% guarantee promotions of late will continue; b: promotions will definitely be available during the time frame you'd like to go to WDW. Free dining in late August is of no value to someone who can only take a vacation in early August.
Something else to consider - I believe DVC members get a "cash discount" if they want to stay at a DVC resort without using their points (or take a vacation longer that's longer than your points will allow). I believe the discount is usually 30%. Which means, in theory, you can buy fewer points to still get some of your vacation at a better discount...
THEN pay cash for the rest of your trip, at a discount...
AND - if you're going every year as you seem to indicate - you can use your DVC membership to get the discount on annual passes for each member of your family, which means at least $500 saved one year, AND if you schedule your trips right, no need to pay for park tickets at all the following year. You could also use your annual passes to get annual pass discounts for rooms, if it turns out that's a better deal at any given time than the DVC discount.
And this is less contingent on special promotions like free dining, where you can go when you want to go as opposed to when the discounts apply.
Which means that yeah, you're paying $1869 in your dues for 350 points at VWL. But you could save up to $650 on your annual passes (depending on if they're just park hoppers or include Water Parks/DQ and other perks). Now my math is a little fast-and-loose, and doesn't factor in the usual annual price increases, but stick with me:
10-day park tickets with the Water Park Plus option is $428 per person, 5 people in your family, for two years, is $4280.
Versus $2791 for 5 Premium annual passes that will last you through 2 annual visits, if the second trip begins no later than 10 days before the passes expire.
2 years of VWL maintenance fees at 350 points runs roughly $3738. But you're saving $1489 on ticket prices during that same 2 year period. Plus, you can then buy membership in Tables in Wonderland and save 20% on pretty much all your sit-down meals (including alcohol), but forget that for now. If you apply the theme park savings, then the difference is $2250, for 2 10 night stays in a 1BR Villa.
Just throwing it out there...