My family has owned
DVC for 16 years, and we think it's one of the best things we've ever done. That said, it's not for every one.
DVC is great if:
+You can afford not only the initial cost of points, but also the recurring expenses of dues, park tickets, airfare/gas, means and miscellaneous items.
+You intend to go to stay at a DVC-owned property at least every 2nd or 3rd year.
+You like having a kitchen and washer/dryer with you on vacation.
+You don't mind not having daily maid service.
+You are able to plan 7 to 11 months ahead OR are able to be extremely flexible with your dates and accommodations.
Is booking really easy or do you have to book months and months ahead? I just hate to sign up and be impossible to get the dates/location you want.
Yes. Booking is generally really easy, if you book months and months ahead. There are a few minor exceptions, but for the most part, if you book as soon as you have the chance, which is 11 months out, you should have no problem getting what you want. For high-demand reservations (AKV concierge, BCV/BWV for Food and Wine, VWL at Christmas, Grand Villas, etc.) you should book at 9am on the first day you can. For less crazy times of year (and DVC peak times are different from the peak times for WDW in general), any time more than 7 months out should be plenty to get you a room at your home resort.
If you can't plan more than 7 months out, prepare to spend a lot of time at Saratoga Springs and Old Key West. These resorts, while lovely in their own ways, tend to fill up last because of their size, location, and understated theming. If you are happy to stay anywhere on property and wouldn't mind SSR or OKW, then booking in the 3-6 month range may work for you.
DVC also works pretty well for last minute, one or two night getaways, which you might be able to take advantage of for the new DVC Hawaii resort. When I lived in Florida, 90 minutes from WDW, I'd frequently call in the morning to get a room for that evening, and I always got something. With there only being the one resort on Oahu, it may be more consistently full, but you never know.
Phew, that was long. I hope that helps.