It is certainly not a lost cause.
If your primary destination is WDW, you are content to stay at any of the WDW properties, you can book six months or more out, you will always find SOMETHING at WDW. If you book a home resort you enjoy, and book it before the seven month window, you will always have a resort to stay in at seven months. At seven months you can switch. See what's available. Sometimes, nearly everything is - more often MOST things are, and very rarely during the year very little is.
If you are the type of person who decides that this year they NEED one of the few VAKL concierge rooms and you don't own there, or think that an annual F&W trip where you stay at an Epcot resort is in the cards - when SSR is your home, you are doomed to disappointment with
DVC. While its possible that you'll always get exactly what you want when you want it, it isn't very likely.
The more flexible you are - the more you are willing to take resort X instead of resort Y, to travel in early September instead of October, to jump on VGC or Aulani when its available instead of planning a trip a year in advance and then finding it booked - the happier you will be.
I think the the worst is the offsite resorts - each of them can be challenging to book at certain times of the year (for California, its pretty much year round) and as they are the only DVC option at those locations, it can be really disappointing not to get your room. Whereas with the onsite resorts, most of us buy to take multiple trips to WDW, and if you don't get BCV this year, you can try next year.