Thoughts on my March strategy?

Do you have spare points to book rooms? If not, it might be difficult to find 5 consecutive days. The problem is that if only one or two of the 5 days show up, you would be put in a position where you have to be roomless or wait for the other days to show up. If you wait, then those days could disappear. I would try breaking your reservation into 2 or 3 day chunks at most. Then you can replace them with days that you want at the other resort. You'd have to be OK with the potential of having to move a few times, even if it's likely that you'll be able to piece together the reservation (and not have to move).

My guess is neither will be fully available af 7 months. Youll have better luck with stay 1 at AK, but 5 consecutive nights is a lot, esepcially at a very popular time.

If you’re willing to book 1 night at a time, i rhink youd have a good chance of getting it done over the course of the entire 7 month window. BruinDisney’s strategy is the right one- it works best if you have extra points and can be flexible. If not, you need to weigh what is your priority- getting consecutive stays for the trip vs these specific locations.

If you want to go for it, id start by booking whatever is open at 7 months, then making wait lists for individual nights. Stalk the system, and as you add nights, make new waitlists. You can then call member services and have them all merged into one booking. The downside/risk is you could get to March and only have 3 nights of one of the stays, and 4 of the other, etc. if you dont mind changing rooms 3+ times during the trip then itll be relatively easy to get done. My guess is you can probably get Stay 1 done over the course of 7 months, Stay 2 will be the “?” But is possible for sure.

So you guys are suggesting dual booking essentially? Keep my original booking in place until I've secured all 5 days of each stay.