Seems quite nutty to think you’d find yourself flying to Hawaii twice per year even if the housing was free
Personally, I'd be more likely to do a two week stay than two one week stays, I'd rather reduce my time on an airplane. But leaving for two weeks is harder than leaving for one for all sorts of reasons.
There are certain trips I try to do annually but I have zero interest in being locked into someplace like Hawaii on a schedule.
I agree that, especially, after semi-retiring, my goal isn't really to travel less but to spend less time on planes.
Odds are you're just staying with tourists most of the time, and whenever you do need to deal with the locals you have to ignore their thinly-veiled contempt mixed with self-loathing for depending on your patronage.
I hear it gets kind of awkward for Paris people getting summer homes in Britanny. I'm pretty sure the degree of hostility towards mainland Americans getting winter homes in Hawai must be much higher.
Also tourism economies are terrible and create a bunch of terrible perverse incentives for both business and government.
Source: Grew up in one
Obviously, not every worth buying a timeshare.
Of course none of it is as easy as they make it sound.
I do go up to my dad's--now brother's--place in Maine a few times a year but that's as much for family as having a need to go to a specific location. Absent family, I'd probably even vary that a bit.
https://en.wikipedia.org/wiki/Razzle_(game)
Where they actually cheat to help you get enough points that you think you could win them when they stop cheating the game is unwinnable. If the cops show up they will see the carnie playing ‘honestly’ and not see anything wrong. In terms of psychology it is the king of scams.
In the case of the timeshare schemes you will find all sorts of problems and limitations when you try to redeem your points, it is like the limitations on airline frequent flier points but raised to the Nth power.
A beach hotel starts at ~$300/night.
In the end, the best case a timeshare does save money. However for most people the restrictions mean you are never in the best case and often you are in the worst case and lose money.