First of all, welcome to the DIS boards. You've definitely come to the right place to get your
DVC questions answered.
I am confused about the booking window. Am I to understand that I am going to have a difficult time getting into one of the WDW resorts if my home resort is HH?
I wouldn't say you will have a difficult time as long as you are flexible as to which WDW DVC resort you stay at. Also helps if you are somewhat flexible with the dates.
Home resorts get to make reservations at the 11 month window prior to a reservation check out date. Everyone else gets to make reservations at non-home resorts (in your case, any WDW resort) at the 7 month window. So yes, at certain times of the year it can be a challenge to get a reservation.
What you will often hear on this board is to "buy where you want to stay the most". If you want to stay at WDW primarily, most would advise you to purchase a WDW resort. If cost is your main concern, you might want to look at OKW resales...they also have the lowest annual dues....and you would have an on-site location that you could reserve at the 11 month window, and switch to another location if you wanted to at the 7 month window.
If you're going 5 times a year, I'd definitely purchase an on-site DVC resort at WDW. Just my opinion.
Also, on the banked points. How long are they banked for? Do they expire after a certain time if I don't use them?
Points are given to members on the first day of the month that they have for a use year. So a February use year gets their points for the year each February 1.
Once points are banked from use year 1 to use year 2, they must be used by the end of use year 2 or they expire and cannot be used ever.
BTW, the same rule applies to borrowed points. If you borrow from use year 3 to use year 2, you have to use any borrowed points by the end of use year 2 or they expire.
I don't know what perks came with your package, but if you don't think you'll be going to HH much, I don't think it's a good fit for you.
Good luck in your decision. And ask more questions!!