Hi Gina,
I have wait listed multiple times but am no expert at this so please someone correct me if anything is wrong here.
First thought - WDW resorts should be easier to get into in late July than HH, but I wouldn't want to wait to long to find out anyway.
The wait list is active until 31 days out I believe and then you'd have to call and tell them you wish to remain on it. That will last until 7 days out. Since we are within the 7 month mark for end of July that key point has passed. The next would be the 60 day mark, followed by the 31. Those are times when people move due to II trades and wait list ends etc.
If I understand your plan it is either that time frame in HH or that time frame in WDW? I am not sure about the availability of late July at WDW, not having tried it before. You might be safer - accommodations wise to book the stay at a WDW
DVC resort and waitlist your trade to HH. At least this way you'd have accommodations for your vacation.
It still leaves you wondering where said vacation will be WDW or HH. It also doesn't help with airfares, dining reservations etc. But at lease you'd have rooms!
The other pitfall is no doubt you'd have to start your wait list over again if you book a WDW resort now. And the point difference would also be an issue depending on if the waitlist came through and what status any remaining points would then be in. (If the WDW resort is more points than HH and the wait list comes through are any remaining points still bankable etc.)
I am not sure if this helped at all but PD to you

however you decide to work it.