Subscribed. We're considering a house along the coast in the next few years. I agree with @Brew that this decision really depends on what you want out of the property. If you want to show up once a month, drive a four-wheeler and shoot .22s, and build a campfire, but otherwise have a "lock and leave" setup, this may not be the right decision. If you enjoy working on projects (especially if you're buying something that needs work), and you like to tinker with tractors, build shit, etc, then hell yes! Go for it.
From our perspective, we're going to look for a stand-alone house, potentially even doing new construction. I have a special needs kiddo, so we have some specific requirements for him that can be tough to achieve in a condo setting.
Referencing the Smithville / Winchester area specifically, my uncle, his brother and his dad bought 85 acres about 10 years ago in that same area. All three of them live in the Richmond / Rosenberg area, so it's not a bad commute. Already had a nice house, pond and barn. The three of them get along great, and they (cumulatively) still use it constantly. Heck, they've bought two tracts of adjoining property since then and now have about 150 acres.
Here's the caveat. My uncle has three kids, two in HS and one in college. He's up there MAYBE twice a year at this point. If this was his and only his, it would've been sold within two years of purchase. But, his dad and his brother are up there damn near every weekend. They're now running cattle, and constantly working on projects up there. His dad is retired, and his brother works a flexible schedule with both of his daughters are out of the house, so there's plenty of time to handle all the chores around there.
One con... About two years in when my uncle's brother and dad were still working quite a bit and none of them had as much free time to get up there, they hired a local kid (late teens) to help around the place. Good kid, worked hard when they were up there. He'd help with the cows, fixing fences, etc. They trusted him, and started having him take care of things while they were gone as well. He ended up falling in with a REALLY rough crowd and got talked into hosting a multi-day party / bender at my uncle's place. End result was being robbed of all electronics, guns, tractors, equipment, tools, etc. Longer story to go along with it, but they literally caught them dousing the exterior of the house in gasoline and were less than 10 min from him putting a match to it and burning it to the ground. So, if you do outsource help, consider that can be a rough area and good help is always hard to come by.