The 7-month window works best when you can go to WDW during non-busy times. However, also be aware that the lowest seasons for WDW are not necessarily the lowest seasons for
DVC. Low WDW seasons are actually a popular time for DVC members because of lower point costs.
If you want to go to HH as your primary resort and maybe go to WDW every 3rd or 4th year, then HH would be OK. But if you really want to go to Orlando a lot more often, then you'd probably be better off purchasing there. (VWL or a resale at OKW, BWV, or wait for BCV)
Remember though, if you purchase a WDW resort, then you've got the 7-month window at HH which will pretty much close you out of any summer time at HH.
If you have further questions, you can post back with specific timeframes that you would most likely want to go to HH, or WDW, and if WDW, which resort you would prefer. Members here can then give you more specifics on what those timeframes might be like in regards to 11-month or 7-month windows.