I've done at least 10
DVC trips since buying in 3 years ago...only two at 11 months out; maybe 3 or 4 or so at 7 months out. The rest have all been shorter lead time than that. Three were "last-minute" for very busy times--(Thanksgiving, booked in late in June; and two spring break trips--one only 10 days prior to the trip; the other 6 weeks prior)...
It can work--and in fact, to date always has for us--if you're willing to call frequently, wait list, pay cash for a night (although twice I reserved for cash but wound up getting the villa on points prior to checking in), and use the wait list. I think the key is being willing to stay anywhere (for two of our really last-minute trips we wound up at SSR and OKW--both of which we love; this latest spring break trip, which I started booking the last week of January (for a March 15 arrival), I got all five nights at BCV! Didn't get them all at the same time...started at OKW and then switched to BCV for two days, then another two days, then the last day (with the last day "in the middle"--but we decided we would be willing to move if we wound up not getting the nights at BCV). It also helps to be willing to "strike out." We haven't yet struck out, but all my "last-minute" trips were begun with the "warning" (to my unwilling (or unable) to plan college son) that it might not work out...you also need to be willing to reserve a day or two at a time, and keep waitlisting/calling back to fill in the nights as you go...it's rare for multiple consecutive nights to open up all at the same time...
This would make me crazy if all my trips were planned 2 months or less from arrival...but most of our trips I can book considerably further out than that...and our "guaranteed" annual trip--T-giving, I book at 11 months out. So if you know you can book 11-7 months out (or even 6 or 5 if you like one of the bigger resorts) for at least some of your trips, the hassle factor of putting together a last-minute trip may not matter so much, especially if it turns out for you, as it has for us, that it's very doable...you just have to be patient, persistent, flexible and willing for it not to work...
Hope that helps...