That's a fun story! We, too, have been considering adding on HHI points (we've owned at VWL for about 15 years). Here are some random things to consider that cropped up while I was reading your post:
- While age should be a consideration, statistically speaking, you should have quite a number of years left to enjoy
DVC. I can't answer for anyone if the cost of DVC is worth it based on remaining years either of life or of a particular contract, however.
- Remember, HHI has some of the highest dues of any resort, mostly due to the nature of its location which is often, certainly in the past few years, in the middle of hurricane alley. Those dues will go up each year, some years quite sharply, so just be prepared to pay those for the remaining years of the contract.
- I agree that in many ways, a vacation at HHI is far better than at WDW. Still, it's worth noting that at some point(s) down the road, your family will likely want to go back to the World. If so, then owning at HHI will only give you the 7-month booking window which could be problematic during numerous high demand times. Even so, there are usually rooms to be found at SSR, OKW, and often AKL except during really tough to get windows such as the holidays, for example.
- If you love HHI (obviously you do), then I'd rather have the 11-month booking window there and 7-month at the World than, say, owning a WDW resort and trying to get in to HHI at 7 months during the summer or spring break.
- Resale vs. direct is something to study carefully. With infrequent exceptions, buying resale is going to cost you far less than buying direct from Disney. I mean thousands of dollars. The perks of buying direct from Disney do NOT offer you enough savings to make it worthwhile, especially since said perks can be withdrawn at any time as they have through the years (e.g., free valet parking). Now, if you want the cachet of owning a blue card and having those perks, then that's your business and more power to you. Just know that you will likely be leaving thousands of dollars saved on the floor.
- One of the things you lose with buying resale is that you wouldn't be able to book any of the new resorts currently in the queue, such as Riviera and Reflections. Still, you will be able to book into any of the previous Group of 14 which offers quite a library of wonderful resorts.
- Some people opt to buy a larger contract resale, then go with the minimum buy-in of points direct. That direct buy then gives you the perks and allows those direct points to be used to book the new resorts.
- Finally, in terms of advice, be wary of buying a large contract. They work fine, but should the need arise to sell it down the road, they are harder to unload and generally fetch lower prices on the resale market. That's why you often see 400+ point contracts languishing on the resale sites. Although the cost per point is cheaper, multiply that cost by 400, 500, or more, and the contract becomes quite expensive. Many opt to buy a couple of smaller contracts (same Use Year is wise) in case they want to downsize later, say when kids have grown and flown the coop.
Best wishes to you! You're smart to do research. Many don't.