I think what finally made me take the leap was seeing how many rooms seem to be available late at SSR (like 3 to 4 months out at off-season). Even though so many refer to it as the "resort of last resort", it seemed to me that if you bought in at SSR, all you'd really get was an 11-month reservation window at a resort that seems to have openings much of the time anyway. Obviously, that's not near the case with other resorts on property, and we're specifically talking about off peak periods for sure, but if there's at least a really high likelihood of having availability at SSR "as a last resort", then that's a pretty good safety net.
Again, it's a combination of preferred seasons, a desire NOT to book studios, and a pretty free flexibility. That's absolutely not the case for most, but it looks like it will work to my benefit.