I have only been an owner since June.. But, I have found it to be not too bad as long as you are flexible.. For our first trip, I did plan 4 nights at OKW in a 1 bedroom- this was booked in June for late july stay. BUT, I did decide to start this trip a day early and was able to book a 1 night stay at AKV while I was driving on the way for that night. Also, I was able to add a day at OKW at the end- just called that morning when we decided to stay longer..
I am planning a solo trip In Oct. I had booked a BLT studio around August but my dates changed and when I called to cancel I was able to get a std studio at BW ( during F&W) for 2 nights. This was done around Sept 1st for stay Oct 26-27. Now, I have been trying to get a WL for BLT and that hasnt come through but I am quite happy with BWV for F&W.
Now, we live in Arizona and realizing on this past Thursday that the kids fall break and hubby's days off converged. We have decided to do a quick 3 day trip to DL.. Now, I did want VCG but not available but I was able to book 2 nights at the Paradise Pier hotel using points... The 3rd night we left open because we may go to San Diego.. This trip was booked 5 days out..
So, IMO, if you are flexible, it's doable.