I think we were pretty well prepared by the time we bought in, in large measure because of the help we got here on the DIS.
As a result, we've had no problems administering our account, despite the fact that we have three families using it...two of whom book only on short notice. I have to say that Caskbill's FREE DVC planner has been a wonderful addition to my desktop, and I don't know what we'd have done without it.
Surprises? I can't say
we've had any nasty surprises, but I sure have seen a few.
The one that still puzzles me is the situation people get themselves into with distressed points. Sometimes those are caused by unexpected and unavoidable cancellations, but
I've been amazed by the number of people who don't understand the bare basics of DVC account management -- banking, borrowing, cancellation policies, holding account, etc.
The other thing that has surprised me in a negative way is the
difficulty folks routinely have
with friends and relatives as guests. We seem to have one gut-wrenching saga a week about how BIL has cancelled at the last minute, leaving the DVC owner in a huge lurch. Without the DIS, I would just assume everybody would be so blown away by being allowed to go to DVC that they'd be the perfect guest, but that's obviously not so.
That said, we treated Grandma and Great Aunt last December with zero problems and it's been the nicest thing we've done in many years.
Good surprises have been many. The DVC Annual Pass is not a biggie for us, because it's only $25 off our Fl resident price, but it's a very nice savings for those who don't live in Paradise. We'll actually probably switch to the seasonal passes when these expire because of our visitation pattern, but the AP discount is BIG for most DVCers. We are now
DDP fans, so we're glad we can get that (couldn't when we joined), although we had DDE before that.
Our biggest and most enjoyable surprise is our ability to
slow down our WDW vacations. We've kinda commando'd everything by now, so DVC lets us slow down and actually relax. Last trip, we had a tough time getting DD4 out of the OKW pool to go to theme parks (despite the fact that we have one, and she also goes to swimming lessons twice a week).