Going along with the premise of 'so long as you are happy where you buy', I did some very rough math to get a picture of what per night it would cost to spend a night at SSR, Boardwalk or Riviera, taking into account the price paid per point and the first year dues on that contract. I divided the contract by the remaining years to get the cost per year - hence the very rough math and no accounting for paying almost double if financed through Disney. (Don't finance = bad idea for a luxury product). This is all for the first year of a contract. A lot of things vary and dues go UP. Over the lifetime dues will be your most expensive contract cost.
So, it really all comes down to where you want to stay and what you are willing to pay for that experience, taking into account location, luxury of accommodations, theming, dining available and anything else that makes your stay valuable to you.
My rough numbers gave me for a preferred view studio in summer Jun11 to Aug31:
SSR paying $105 per point- about $175 per night
BWV paying $120 per point - about $225 per night
BWV paying $140 per point - about $240 per night
Riviera paying $195 per point - about $311 per night
For me it comes down to how long a contract is useful to me. My contracts will all expire when I'm 88 years old. I see myself getting myself there for the next 10 years, and depending on others to get me there after that.
A lot of people talk about bequeathing the contracts to their children. May work some of the time. May be a burden the rest of the time. 1 out of 3 of my children are interested in
Disney vacations after 25 years of Disney vacations, 20 of them DVC. And that's only every couple of years. Most of the time I go alone or with friends as guests. Just my experience - they have worldwide interests to spend their time and money on. Disney is free for them.
So, if I were buying now and was 35 to 45 years old, and earned a moderate income (and actually able to afford DVC without borrowing or financing) I would buy SSR and try to get something else at the 7 month window.
If I had more disposable income and liked Skyliner and a more upscale room - maybe Riviera - if over $300 a night was the norm for a yearly vacation at Disney.
Middle of the road - 45 plus to 60 plus years old - do whatever you want - you should have the money to purchase and should know by now what you want.
Just a simple assessment. As far as ownership, if you are buying to take the grand kids, wonderful! If you are buying to GIVE it to someone else - rethink that. It's a gift for some, an obligation for others, and may be worth less than you think when they are trying to unload it.