Welcome to Tug! You're in the right place to learn more than you'll ever think you'd want to know about timeshares, and the timesharing process.
Take things slow, and do your research. It is MUCH easier to get into one than to get out of one. Read all the sections about buying and selling a timeshare, until you feel you have a clear idea of what appeals to you. Visit them (but don't buy anything!!) to get more familiar with the different programs. As David suggested, rent a timeshare from an owner to get a feel for how it differs from renting a hotel room. Depending on where you're staying the differences can be enormous.
For example, hotel rooms tend to be one all-purpose room, have tiny microwaves and mini fridges, and little else. Timeshares tend to have separate bedrooms, multiple bathrooms, full kitchens and washer/dryer units right in the room. It's more like staying at an apartment, than a hotel. But that also means you aren't usually treated to daily maid service, trash removal, and someone to pick up after you. It's a trade off.
If you like feeling relaxed and "at home" when you travel, if you tend to stay put for a few days or a week at a time, even while seeing the local sites, and if you like the convenience of being able to cook for your family to enjoy meals in, then you'll begin to see the advantages of timesharing, vs. renting a hotel room.
Cost can be a factor. If you have a seriously limited budget, or don't stay more than a night or two at a time in one place, timesharing may be too expensive for you. Points programs let you schedule a few mights at a time, if you wish to break up your vacation into smaller pieces. But the associated costs may be something you'll want to be clear about, so you don't spend more than you need to.
No matter what you get, buy it resale! There is nothing worthwhile to justify spending thousands (or tens of thousands) to buy from a Developer. The savings can be monumental - a "second hand" ownership can be as low as $1 or less, compared with ten or twenty or thirty THOUSAND dollars if purchased "new." But when you stop to think of it, even that brand new timeshare will have been used by someone else before you get to use your time there. Avoid the depreciation, and buy in resale. It'll make your "per night cost" much, much lower.
Maintenance fees are a factor to be considered. You need to weigh the cost of the ownership against your intended use of it. If the maintenance fees are too high, and you can rent the same or better place for less, then it's not a good idea. But if the cost is average (or below average) and you have the option to stay at a place you like without paying too much, then it's probably a better deal, and worth looking in to.
Gone (mostly) are the days of the mysterious "tiger trader," where a cheapie timeshare in some obscure place will let you trade in to the top resorts elsewhere. They do still exist, but they are not too common. The general rule now is to buy where you like to stay, rather than exchanging through a third party company. Exchange fees drive up the cost of your vacation, so you need to weigh into what works best for you.
My recommendation would be to look into buying a points program of some sort, or one of the "mini systems" of internal exchange groups that own in several locations. So you'd trade within your own group. Only you can decide if it's worthwhile, and whether you think you'd get your money's worth.
In my own example, I like to vacation in Hawaii, so that's where I own. I have a week's stay every two years in a nice oceanfront unit in a pleasant resort. My costs are less than half of the price for a similar-but-less hotel located right next door, that shares the same beach as my resort. The math works well for me. But your situation may be different. I bought my unit resale, and spent less than $500 including closing costs for the whole thing.
Good luck in your research. Join Tug for $15, and learn what you can. It'll be the best vacation dollars you ever spent.
Dave
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