It's really great that your focus is on including everyone and prioritizing that they all are able to come and enjoy regardless of budget. I guess that most people would think, well they are getting free accommodations, the least they can do is x, y, or z.
I think my Military AND Medical training drilled into me the idea of subliminal messages. I recall an episode of MASH where Winchester gave a box of specialty chocolates to an orphanage then found they'd sold them with the message being it doesn't make sense to give someone candy when they don't have food regularly. Plus having grown up poor there is a particular school trip where funds were not sufficient to eat each meal when I was in High School.
Using timeshares with full kitchens must help here as even free accommodations at a hotel can expensive for people when you need to eat out every meal.
Timeshares fit my personality. We rarely eat out on our family trips but when it's just Kim and I we'd likely eat out most days once each day.
Also choosing HHI, and Grande Ocean in particular, while I've never been myself (at least until October) it seems like the island and resort itself is more than enough to keep anyone entertained all week that doesn't want to spend money on additional excursions, other than perhaps the cost of a bicycle rental. Is everyone in your group within driving distance or do people fly in for it as well?
We think so, it's our favorite resort and HHI is the closest MVC to the group in general. And it's a good resort to get people close together with that many units.
I do wonder, did you just keep buying more weeks and inviting more people, or did people start hearing out about the trip and indicate they would like to be included and then you bought more weeks to accommodate?
A little of both. We kept adding weeks and expanding our invitations to a wider array of family. Early on we alternated between mine and Kim's side with a core group for each year. Now we have enough to include everyone from both sides that I would consider core and then a little beyond that. I think we're done but including this last purchase that I'm waiting to finalize.