Sorry for the long response. I’ve been reading IE for 10 years now but never post. This topic I will say I have some personal experience with.
It’s great you are open to the idea of timeshares as they seem to potentially fit with your lifestyle. Disclaimer: I have attended a few presentations (Worldmark/Wyndham, VI, etc) and have a friend who used to work in the industry. I have done way too mu. Research into some of the companies and almost bought. They, in themselves, are not evil but very misleading. There are many benefits for most aside from just the usage of points for the 1-2 weeks you get (last chance vacations at deeply discounted cash prices but difficult availability unless you are very flexible, exchanges like RCI, etc). Keep in mind they will say that X points will get you 10d-2weeks in a multi bedroom unit but once you actually look at what each unit truly costs during normal vacation periods you will find that it often translates to far less than that. My friend said a “10d-2wk” point package usually actually equates to 1 week a year or 2-3 every three years actual usage.
I would HIGHLY recommend looking at the secondary market if you decide to go forward. Redweek for one has many deal which will net you the same number of points for around 1/10th the cost of upfront points. There are a few perks you won’t have unless you buy from a developer but most rarely use them. These markets are used by the massive numbers of people trying to sell their timeshares. There are some scams out there on these sites but it doesn’t take much to identify them.
Once you mitigate the huge upfront cost then you are simply left with the maintenance costs which I look at as a monthly contribution to a vacation fund. Keep in mind, you need to account for the fact that these maintenance costs go up like clockwork annually at a rate of 4-5% usually 5%. This isn’t from me this is from my friend in the business. So these are not really shielded from inflation. I calculated my quoted maintenance fees assuming 3% increases annually and in 20 years my $80 fees were something like $4-500 (it was long ago so unclear on exact number). This is not something I wanted to pass along to my kids (they could always sell it I suppose). A partner of mine at work did buy into DVC and has fixed MFs for life but this is an aberration but an amazing deal for her.
Also would highly recommend reading some of the forum topics from a timeshare owner forum. They saved me $30K when I bought them cancelled Wyndham.
https://tugbbs.com/forums
Should you decide to move forward I’d look into Worldmark if you’re an East coast guy. My understanding is that the Wyndham/Worldmark partnership was done for expanding WM’s Reach into the west. Think Westcoast = Wyndham, Eastcoast = Worldmark. This is way oversimplifying it but a rough idea. I’m a wescoast guy so Wyndham was a great option for me. I bought the same number of points that we almost bought from a developer, when points cheap on Redweek for $1200 ($80 monthly MFs) which would have cost me $30K. Happy with the purchase and if I decide to sell later I’m mostly only out the MFs which like I said are simply what I would have put in my vacation fund anyways.
Sorry for my rant but I wish I had know this when I went to the presentations. I did get two free trips out of them but those trips are pretty bad FYI.
