I suspect the biggest "satisfaction" factor is whether or not people actually
use the timeshare they bought. The second biggest factor is whether or not they understood and can afford the financial commitment they are making. If you think about the "help me get out of this" posts we see here, they are almost always one of two cases. One: I bought this thing, but I really can't afford it and I need to get out of it. Two: I bought this thing, and I haven't used it for years, and I need to get out of it.
I don't know what to do about the fact that a lot of people don't (or can't) do the second part. Anyone who is financially literate should be able to understand the terms of a timeshare loan. They also should know that the annual fees are going to go up because inflation is a thing and it exists everywhere. I used to think that this was a failure of education. I am continually shocked at how many otherwise well-educated people simply refuse to even admit that the time value of money exists, let alone considers it when making a purchase. Then again, I am not sure I really understood it until I took an engineering erconomics class as an undergraduate.
The first part also matters, and again, I'm not sure if there's anything to do about this. We've all made purchases that, at the time, sounded like a great idea, but that we never use. A lot of gym memberships and exercise equipment falls under this. But, working out is hard. Taking vacations shouldn't be, but for some reason it is for a lot of people. Timeshare ownership works best if you can have a mindset where vacations are just as important as anything else in your life. Most people in the US fit in vacations around everything else in their lives. We have among the lowest amount of paid vacation per year of any OECD country, and even then a substantial number of people
let their vacation days expire rather than use them.
I am not sure many of us on TUG understand how hard it is for some people, because we "get it." But, there is CONSTANT societal pressure from all around us to work harder. I read an op-ed piece in NYT the other day commenting on the fact that our post-pandemic re-evaluation of our relationship with work, and making work less important, was a BAD THING. My involuntary audible reaction to that is not fit for sharing on a family-friendly web site. It's fine if our "productivity" goes down a little, and stuff gets a little more expensive, so we buy a little less of it, if what we are getting in return is more of our sanity back. We don't need to sacrifice ourselves on the altar of productivity.
Which brings me around to developer purchases. Are they ideal? Of course not. You can often get almost exactly the same thing for a lot less. That doesn't mean that they are terrible. If you can afford it, and you actually use it, maybe it's not the worst thing in the world that you paid more than you had to if it actually changes your relationship to vacation for the better.