I too have good feelings about our decision to enter the world of DVC ownership. My DW and I choose to purchase a 220 point resale at BWV two years ago, it really was a no big deal to do. As a reference we used
http://www.dvc-resales.com/index.htm (sorry if I shouldn't give a plug), the transaction was simple and professional no pressures other then signing over the check. It is true that resales are presented with an "asking price" which is negotiable but first right of refusal is a Disney thing. One area to watch in a resale would be the status of those points, make sure you understand what points are currently available, borrowed or banked.. avoid surprises. Points from a resale are no different from those of a DVC direct purchase in fact your membership card will have the originally purchased date on it.
As far as booking the stays this to has been no problem. We've used points to book at our home resort (BWV) as well as a MK resort (Poly). In fact we've used our points to stay at the BWV two weeks ago, what a great time of the year to go. Keep in mind there are differences in staying in a Dis hotel room (2 beds and a pair of chairs) vs. your home away from home (a small condo). It's real nice to spread out and kick back in your room after a long day enjoying a snack and your favorite beverage (there's a blender in the room, so a nice margarita or daiquiri could even be in order, lol).
Overall the whole point/stay thing is pretty easy to figure out and quite flexible. I am convinced that the program is a fair deal, it's certainly not a "freebie" but we are staying in some of best Disney properties multiple times a year. Sounded good to me and so far it's living up to my expectations.
Oh ya... One more thing.... The real plan for DW & I was/is to start having "adults only" stays, boy Disney can be fun as an adult tooooo!!!!
Question 1: Booking was simple and Disney happy
Question 2: Saved a bunch with the resale... don't believe I gave anything up.
Final thought: Having a DVC may be the thing that makes an annual pass a economical choice be sure to factor that into your decision.