We were where you are for a couple of years. We love the GF, the Y/BC, and the BW, and for many, many years have stayed where we could either ride the monorail to MK or walk to Epcot. We almost always got either two rooms or a suite, as my mom likes to travel with us. We have stayed Club level for years; they built it, we came.
By the time you added in taxes and fees (don't forget to add them in when crunching your numbers), we were averaging more than $600 a night per trip, before you take dining plans into account.
For us, SSR and OKV are not selling points, they are fall back positions if nothing else is available. We want easy access to MK or Epcot, or we want a one of a kind experience like animals outside your room. (The lure of AKV for us is savannah view and club level.) That said, we enjoyed using our developer points at SSR. My DM and DSF are big golfers, and as a golf resort, SSR is perfect for them. (If they ever do a no-parks golf vacation without us, they will almost certainly choose to stay there again.)
As far as the advantage of being able to dine in the room goes, DH, DS and I left snacks and drinks (including wine) in the room, and treated it like Club level. We did eat breakfast every morning there, but we ate every lunch and dinner out. My DM and DSF also ate breakfast there, and had a couple of late lunches and dinners in the room as they brought bread and fancy cold cuts along. Where we saved the food money was in buying the discounted APs, then getting the TiW for the first time. We love V & A, and we more than paid for our TiW with a dinner for two with the wine flight. We almost exclusively do TS restaurants, usually signature dining, and the TiW card saved us hundreds of dollars.
We are very solidly in the "wish we had bought sooner" camp. We did buy where we want to stay, which is very good advice. We would have been happy with BWV or BCV, but we knew we needed an Epcot resort. We bought AKV so we could always get SV, and would have a shot at Club level. We will probably eventually buy at a monorail resort, but CR/BLT is my least favorite of the monorail resorts. I hope they'll add either a Poly or a GF DVC in the next few years. If they don't, we'll probably buy a handful of BLT points if we consistently can't book it at the 7 month mark when we're hoping to go.
For us, it wasn't a matter of not being able to afford going to a deluxe resort annually. We could, we did. But in this uncertain economy, and even before it got this bad, we recognized that what we could afford to do now might not be the same thing we could afford to do 5 years from now. We hope we'll be living as well, or better, in the future, but we don't have a crystal ball to let us see for certain. With DVC, we know we can go to WDW for the next 40+ years no matter what else is going on in our lives. If there is a year we don't want to go, we can bank the points or use them somewhere else. I certainly wouldn't call DVC an investment, but I would call it vacation insurance. For us, it was the right decision.