I think the smart money for you would be to rent a timeshare in a town you like, and compare the experience to staying in a hotel in the same part of town. You can decide for yourself whether it works for you, and how you enjoy vacationing.
For me, the space, convenience, and comfort of a timeshare makes a hotel very UNappealing. I like having a kitchen, a full-sized fridge, the ability to cook meals, and so forth. Having laundry inside the unit means I can pack lighter, and save money on baggage fees. Having a bedroom separate from the living area means I can stay up late, while my spouse hits the sack early, and neither of us is inconvenienced. It's like having my own vacation apartment.
As to purchasing, in my experience buying all my timeshares resale, the real ongoing cost of ownership is the maintenance fees. Because many timeshares can be had for $1, or less, about the only acquisition cost is the paperwork fees to change the deed. Many sellers will also pay those fees, so you can get into owning a very nice timeshare literally for free. You need to be cautious about what you buy, because not all timeshares are created equal. And it's very easy to get into owning a timeshare, but may be quite difficult getting out of one. Take your time, do your research, and know what you're getting. It can be great, if you do it right.
I own an oceanfront 1 bedroom/2 bathroom ~1000sf timeshare in a modest-but-comfortable resort in Hawaii, called Kauai Beach Villas. It has an unobstructable 180-degree ocean view, and is located about 100 feet from the water. Living room, full kitchen, dining area, free laundry in the unit, large master bedroom, and two bathrooms. Sleeps four very comfortably. I got it on eBay for less than $100 about ten years ago. I can reserve any week of the year, including holiday weeks, without paying extra. The 2016 maintenance fees were $1223.00 for a week, which is roughly $175 per night.
Contrast that with the high-end Aqua Kauai Beach Resort hotel on the same property, that rents a 320sf oceanview room for $370 per night, plus taxes. Holiday rates are higher. A week there would be $2590, plus taxes. No kitchen, no laundry, no separate bedroom, only one bathroom. True, they do have a great swimming pool complex, but timeshare owners can use the hotel pool for a modest daily fee.
You'll need to make up your own mind, but I can assure you, after you've stayed in a timeshare or two, you'll never want to go back to a hotel. It's a very different experience.
Dave