We have a gulf front timeshare in Treasure Island Florida (south of clearwater) we go to for one week every February. Its a fixed week in an owner incorporated property, not some kind of RCI or other vacation thing. Meaning we are actually deeded 1/52nd of that actual condo on specified dates every year, so it is actually a second home to us, albeit just one week. We absolutely love it. We stayed there during covid year because the Canadians all couldn't come and they were renting all of their weeks that winter and we just randomly stumbled upon it. We loved the area and the people so we kept in touch and ended up buying a week when one of the extremely rare 2 bedroom units came up for grabs. Many of the people have been going there for 20 or 30 years and have slowly collected enough weeks in the same condo that they became full on snowbirds that just started out on vacation years ago. They literally are neighbors to us when we go there, they've seen the kids grow up a lot each visit over the last 4 years. The area is low density because Treasure Island is actually its own sovereign city, unlike the surrounding barrier islands that are all in name only but are actually governed by the county. Therefore they have their own council and ordinances and have mostly kept major high rise development off the island. Our place is a classic 50s style two story motel with a pool/courtyard style layout that they converted to condos in the 80s. Some have been torn down around us and rebuilt bigger, we've already seen the time lapse of one of the run down ones suddenly be a pile of rubble one year, to a a six story block shell of the building the next, to a completed complex peddling $3 million condos this this year, but most places nearby are just like ours.
As much as we'd love to, living and maintaining a beach front place permanently isn't likely to be financially feasible. I'd love to move into the area but somewhere inland in a few years. You can always drive to the beach, and even if we live there I'd still keep the timeshare week as a stay cation or to have friends from home or even the kids down as adults for vacation if they're somewhere else. By then we may even have it longer if the people before or after us ever decide to sell their weeks.
Do what you said and try it out for a month. We just do our single week, but we've met people older than us that have started small as well and have extended their stays in the time we've known them. If you love the beach life give it a shot! A lot of the independent condo/timeshare properties are actually rather obscure if you try to search for them on google and generally don't appear on travel sites, but if you're at all interested in the treasure island area I can let you know about some that generally have rental programs for owners unused weeks.
