We joined in 1993 on our first trip to WDW with our son (who was 7 then). My wife and I had been a few times prior to that, but this was the first time we stayed on property (at CB), and when we saw the DVC storefront (tucked away off to the side of Main Street) we went in. It was our last night and we made and appointment to visit OKW the next day before our flight. We bought and have enjoyed watching our son grow up at OKW from each visit to the next.
We are also taking a family of friends with young children for their first WDW visit this coming January. It gave us a great excuse to book a GV at OKW!
The best experience with a CM was really weird. In 1995, the second year of the WDW marathon, there was supposed to be bus service from OKW to the start at EPCOT. Back then the marathon, like DVC itself, really WAS a well kept secret, and putting the two together created the perfect storm. While 6-8 runners waited at the HH, no buses ever showed up. We could hear the announcements coming from the race start, and we were getting nervous (well, we were probably already nervous anyway, but this was like a bad dream when you just can't get to school on time).
Finally, the CM at the front desk came out, got a DVC van and we all piled in. He drove us to the start, which was way above what we had been pleading him to do for us (which was just to call a bus for us). Funny thing was we didn't know that year Disney changed the start line from where it had been the first year, which had been inside the EPCOT parking lot. Turns out we could have walked to the new start line in an=bout 15 minutes, but we didn't know that at the time. It probably took longer driving there!
I actually found a card where I had written down this CM's name just a year or so ago. I hope he's had a good (almost) 20 years since then.