Is the DVC setup such that no matter how many resorts/rooms there are it will always be about the same difficulty to make a reservation? I'm asking because though some room types and seasons book up right away we have had good success when we are flexible and even when we waitlist.
DVC is not set up so that there will always be the same difficulty (or ease) to make a reservation. A point system that allows any member to choose any time of year to go is, by design, something that can create availability issues during higher demand times of year. You are aware of some seasons that are harder to get than others and all Disney needs to do in the future is create new events or change dates on old ones to effect major shifts in "seasonal" demand. When DVC started Oct was one of the least demanded times of the year. With Food & Wine and additon of month long Halloween events, it eventually became one of the highest demand times. Time beginning the Friday after President's Day was a very low DVC demand time until Disney created the Princess half marathon for that weekend and now that weekend is the highest demand time between mid-Jan and mid-Sep. You could easily have a dramatic shift in DVC demand tomorrow if you woke up to an announcement by Disney that it was changing Food & Wine to February and March.
Disney can also quickly change demand by reallocation of points, which it can do to alleviate over or under demand for rooms or days or times of the year. It cannot raise the total number of points applicable to a resort but it can increase the number needed for some rooms or seasons while doing an equivalent decrease for other rooms or seasons. Five years ago, and over a two year period, it dramatically lowered the number of points needed for weekend nights while raising them for weekdays. Until then, the demand for weekdays greatly exceeded that for weekends year round, e.g., during high demand Oct and during the first two weeks of Dec, it was still fairly easy to find near park resort rooms for the weekend even at 7 months out. With that change, the demand for weekends moved closer to the demand for weekdays, and although for many times of year weekdays are still somewhat higher, demand for a weekend like Columbus Day weekend rose to the point that it is now among the highest demand times of the year. A few years ago, it raised the points needed for treehouses by about 15% year round while lowering those needed for other SSR rooms (all of which needed only minor decreases to equalize total points because they greatly outnumber the treehouses), with the resuolt that treehouses quickly went from being rooms that had become difficult to get at some times even close to 11 months out and nearly impossible at 7 month out to rooms that are now readily available 7 months out, and even beyond, most of the year.
Demand can also change dramatically, particularly at 7 months out, when a new resort is sold. Before SSR, near park resorts at WDW were often easy to get at 7 months out and even well beyond many times of the year. The addition of SSR resulted in its owners having 40% of all DVC points that existed at the time (even today it is almost a quarter of all points for all resorts) with the result that demand at 7 months out for other resorts, particularly BWV, BCV and VWL, increased significantly to the point that anything still available at 7 months out could disappear quickly once the 7 month window opened. AKV has also increased near park resort demand at 7 months out.
Currently the highest demand quarter is late Sep to marathon weekend in Jan and demand for that quarter makes most of the rest of the year seem like a long off season, including for the holidays during that off-season. Though the first two weeks of Dec and Thanksgiving and Christmas were always high demand times, other times in that quarter were less so and demand has increased partly as a result of things mentioned above such as seasonal events and its lower point costs. But it also increased by a change in demographics. In the 1990s and early 2000's, most DVC owners were families who followed their kids' school schedules for vacations. Now, there is a huge contingent of older DVC members, sans children, who can easily go in the Fall at other than holiday times.That shift in demographics will continue particularly now as the population that purchased SSR becomes mostly older adults with children no longer in school, which should intensify the Fall demand even more.
Seven years ago there was seldom a concern about getting a reservation exactly 11 months out except on occassion for BCV and BWV standard view during first week of Dec or time around NYE. Now the issue is arising with several room classes and over more times. Part of that is a just a factor of Disney creating more room categories that are in high demand but low supply. AKV club level studios (and as a result also 2BRs) are the obivous example with only 5 2BR lock-offs and it has issues at 11 monts out much of the year as a result. But the issue also exists with AKV value studios for which there are 20 possible rooms but very low point costs, BLT standard view for studios (and resulting 2BR lock-offs) in particular but also at times 1 BRs and dedicated 2BRs, BWV boardwalk view studios (and 2BR lock-offs) at times, and VGF studios. With VGF, the issue was created by Disney by selling a resort with a very high price per point and points needed per night with only 47 studios, compared to 147 other possible but larger rooms. Most bought enough points to get studios. Studio demand has alsways been the highest demand at any resort but with VGF, it dwarfs the demand for all the other sized rooms combined. We are now seeing elevated levels of competition at exactly 11 months out not just early Dec or time around NYE but during portions of Oct, early Nov, and marathon weekend in Jan. The cause is partly the continuing increase in demand for Fall time. It is also just partly due to DVC members now being far more informed about high demand times because of the addition of online booking and the resort availability tool, and thus more and more are taking the safe course of booking 11 months out or, in the case of some, walking reservations. However, another factor adding to increased demand at 11 months out is the growth of members seeking only studios at all the resorts. During the last 7 years, Disney has dropped minimum required purchases by new members from 160 to at times 100 and even as low as 50. Therre were also over the years a huge number of add-on contracts requiring a purchase of no more than 25 points. Fifteen years ago, the resale market on the internet was in its infancy, and it was difficult for an owner to sell outside of the internet (and that is still true). The internet market has grown over the years to a major force making resales easy to accomplish. The easiest contracts to sell, and ones in highest demand, are lower point contracts. The combination of low point add-ons that could be sold, lower point requirements for new purchasers, and the rise of internet sales of low point contracts has led to more and more owners at all the resorts having enough points to reserve only studios, and it is the excessive demand for studios that accounts for the bulk pf the problem that has developed for reservations even at 11 months out.
Bottom line: do not assume current demand patterns will remain the same. Demand for Fall and studios is likley to get more intense. The times when reservations may be difficult at 11 months out could increase. There could even be a major shift in seasonal demand just by Disney' creating new, or changing the dates of prior, special events. Disney could do point shifts that also cause significant changes in seasonal or room type demand. It could build another SSR and getting anything at 7 months out at near park resorts could become difficult even during lower demand times. Flexibility in time of travel, room size, and willingness to go to wait list should give you the maximum of options but the options that will come through with that strategy may decrease as time progresses.