You raise some good points. Looking at it from a strictly financial point of view, it's a little like buying a house. You buy a $250,000 house and start figuring out when you "break even." Then you have to add in the taxes and insurance and realize you may never break even. Maybe after your 30 year mortgage is paid. But you have upkeep and your taxes and insurance never go away. So why buy a house? It's "smarter than renting an apartment, correct?" For most, sure. You build equity, have a tax deduction and pay the same payment today as you do in year 29 of the loan.
To my point. I own 220 points at VWL. We have owned it for five years after buying from a reseller. We have stayed 7 nights for each of the past five years in a 1 BD vacation home. Now, we could pay cash for the 1 BD which would run about $350 a night + tax. I haven't broke even yet - probably about 2-3 more stays and my initial payment is "even." Like you said I have dues each month (think property taxes and insurance). I also have around 38 years left on my contract. I may sell the contract at some point and make most of my payment back. For now we are content to keep vacationing at WDW. But, I don't have to always go to WDW as I can use my points all over the world at hotels and resorts instead. That's a key also. The other key is - I say a 1 BD home is around $350 per night now. What about in 10 years? 15 years? I'm sure it will be more. I still have my points to use and don't have to come up with more and more money to keep vacationing.
Yes, we love Disney and certainly know they are out to make a profit. Owning DVC has been a blessing in that I can take my family year after year to WDW knowing my largest expense - the room - is "paid for." Financially, it may not be the best investment ever, but then again neither are the cars in my garage of my house that will be paid off in a short 24 years! But it sure is more fun. And keep in mind, promotions like "free dining" are just that, "promotions" that were put in place in the past year to help sell hotel rooms in a down economy. No guarantee that will last, so you can't count on it. But, I can count on staying in some great hotel rooms at WDW for many years to come.