Our goal is to stay here every other summer, so it does seem that HHI does require a 11 month booking window for at least June to August. Maybe I am looking at this wrong, but it seems that it would make more sense to buy in and pay $6000 with MF of approx $600-700, yearly Instead of booking and it costing $3600 or renting for close to $3000. The break even will be after 2-3 trips from rough calculations.
This particular contract was for a closing towards the beginning part of next year so the deed transfer would not occur until after the MF for 2017 are already paid. I would not have to pay until 2018. So I guess it is hit or miss if this is the right move. I buy now, hopefully working a price per point less than $60. Can't really use the contract until realistically 2019 (when I can bank and have enough for a week) or I wait and buy in a year or two - could the prices for HHI go down in a couple years? I kind of don't see them getting higher, but will likely stay stagnant for the more near future until it goes under 20 years left on the contract.
If your goal is to stay there summer you'll probably need the home resort advantage to do it on points, either as a private rental or owning there. I'm guessing you're looking at a 1 BR for 6 nights or a 2 BR for 5 nights and using somewhere around 210 to 215 points for the trip and going every 3 years or so based on what you're posted. Owning 100 points at HH isn't that much of a savings but compared to paying cash it might be enough to justify buying. You're really talking about a savings of somewhere around $150-250 a year assuming mid June to mid August, likely less for early June or late August. Regardless, this doesn't sound like a great contract. Unless it's the perfect number of points and UY and you think you'll have problems finding what you want, I'd pass. The long term plans gives you easy patience but don't let it cause you to make a poor financial choice just because you don't need to use those points. IMO you'd be better off paying a little more and getting a more loaded contract, you can always rent the points if needed. Even with no dues until 18, you'll still be overpaying on dues then but depending on UY, it shouldn't be that much.
I doubt they'll go up but I doubt they'll get a lot cheaper in your timeframe. Since it doesn't sound like you're planning to use these points between HH and WDW both, one of the big plusses of owning
DVC at HH, are you sure buying DVC is your best option for HH stays. Would a different timeshare system or just renting a condo be a better option. You can rent a 2 BR in a beachfront resort for your real costs in this situation, have control, be able to cancel and have significantly less long term risk.
You mentioned break even in 2 to 3 trips, I don't see it. I don't use the target cash option for such comparisons, esp not the non discounted one. In this case I'd compare to both the private rental cost and to the costs of comparable resorts privately, maybe the OF Marriott Properties. Even if you ignore the TMV then you've still got a cost of at least $2000 per trip, likely more in the $2500 range (guessing somewhat because you have provided all that info). So unless the rental prices go up dramatically more than dues, it'd take you at least 8-10 years or around 5 trips to break even (maybe more) and that assumes you'd get a trip close to every 2 years out of 100 points making the best assumptions I could as for number of points, villa size and frequency.
