First step: if you are serious, join the Timeshare User’s Group (tugbbs.com). it’s the disboards of the timeshare universe, and that’s the place to learn.
I think a big source of the negativity lies in the intersection between how timeshare is usually sold and purchased. Some sales agents stretch the truth (or outright lie) but most of them are good at telling a buyer just enough to be factually correct, but in a way that allows the buyer to fill in the gaps in ways that create unrealistic expectations. For their part, the buyer
wants to make this purchase. It is an aspirational purchase that both raises the quality of their vacation lodging and represents an investment in family time and togetherness. And that fuels the buyer’s willing participation in filling in those gaps.
But, if you go in with your eyes wide open—and particularly if you are buying resale and saving real money—then those things aren’t really issues. At their core, other timeshares are just like
DVC (unsurprising, because DVC is just a timeshare): you buy rights to reserve some lodging on a recurring basis, those rights are use-them-or-lose-them in some form, and you agree to pay your share of the ongoing operating and upkeep costs of that lodging and the reservation system, etc.
As for what to recommend: The first question is where do you want to go? If you have one destination that you want to return to over and over again, it makes sense to buy a fixed or floating week at that destination.
But in your case it sounds like you want to go to a variety of places. In that case, I think a points-based system is probably a better fit. But, points-based systems have different strengths and weaknesses in terms of location. So, I think it still makes sense to narrow down based on who has resorts in places you like, and then if there is more than one candidate to decide based on the quality/price tradeoff you want.
The main players are Marriott, Hilton, Wyndham, and WorldMark. You might also include Bluegreen in that set. Those are in rough order of quality/price, from higher to lower, but very rough.
Marriott has a large number of locations, including some international locations. Resorts are uniformly nice, but their ongoing costs are typically on the high end. It is not cheap to buy in, even resale, because the underlying properties have value
and Marriott charges a fee to “wash” resale points. Marriott acquired and is folding in Starwood/Sheraton.
Hilton has a more targeted set of locations: the tend to build over and over in the same set of places (Orlando, Vegas, Oahu, Big Island) but have scattered locations elsewhere. They recently acquired Diamond and plan to fold them in in some way but it’s not clear how much that will cost and whether resale owners can participate. Resorts have a quality level comparable to Marriott in most cases, maybe just a small step down in others, and costs are lower both to buy and to own.
Wyndham is focused East of the Mississippi, Kauai, and the Big Island, but also has a healthy set of locations in the western US. Resort quality is more variable, usually reflecting the age of the resort. The better resorts can hold their own most anywhere, but not all of them are like that. They are significantly less expensive to buy on the resale market (think at most a dime on the dollar), and somewhat less expensive to own.
WorldMark is the “sibling” of Wyndham; they are separate systems, but both owned by the same developer. WorldMark focuses West of the Mississippi, but has some resorts in the East and on Hawaii. WorldMark is a little less expensive overall to own than Wyndham, and the resorts are mostly comparable if maybe just a smidge down the quality level. They are still very nice.
I can’t convince myself to consider Bluegreen; their resorts seem to be in less interesting places on average, the units aren’t as well configured or appointed, but they aren’t different enough in price to make up for those things.
