I also did not try before buying. Bought resale in 2007, with a small contract, then added on direct (both at BWV). I had only found out about DVC in my previous vacation when I took the friendship boat from Epcot to DHS, I didn't know about that either! We (then I was married) got off the boat at Boardwalk because it looked so nice. Wandered around, checked out the public spaces and I loved it. I also recognized that the location was fantastic, waiting for a bus after fireworks, dead on my feet, was one of my least favourite parts of my Disney vacation.
When I got home I did a little research and quickly saw a 60 point resale on the website of one of the sponsors of this board. I snapped it up. My membership has come about in small increments. 60-40-30-50 I know I probably paid a premium for those at the time, but I didn't have $18000 to pay out in one go. I don't regret my decision for a minute. Lately there have been changes that sort of take the shine off, but when I think seriously about selling, I balk. I do love going, I'm glad I bought at BW and BC. The value has increased even though years left on the contract have decreased, what timeshare does that?
I have had many vacations in BWV, a wonderful resort that I would never pay rack rates for (simply because I don't have that kind of money to spend on a room). I have shared it with family and friends, stayed in BWV,AKV Jambo and Kidani, Beach Club, OKW and Poly, got a room for my nephew at BLT, studios for my sister and niece at Vero. All were great stays. That said my favourite is BWV, creepy clown slide and all. If you travel to Disney yearly, and would like to stay in rooms with a little more space and amenities, I believe it is a good buy. Now, at today's direct prices, yikes, I would still advise you to purchase what you can afford to pay for, and add on as you need or want to. If you purchase resale at one of the original 14 you can only stay at those resorts, but there is such a great range of resorts in that group, wonderful locations, and in my opinion better theming, so that shouldn't stop you. As others have said, now more than ever, it's important to buy where you want to stay, especially if you want to experience F&W Festival in the fall.
Good luck with your decision.