You're absolutely missing the point.
This is _my_ fantasy world, not bound by the history of Star Trek; the show itself in later series got ruined by awful writers who couldn't figure out how to make a sci-fi utopia fun to watch and instead made a faux-military/action drama for no reason. I want no part in that future.
Second, I think you actually miss the point of these episodes; the challenge in the Cardassian border wars and issues was "how does a space utopia exist with a (comically) fascist regime?" Debatably, the actions of the Maquis and other border colonies were persons stuck in a land ownership mindset which is exactly what I think we need to avoid. Data even proved this in the episode with the Sheliak to convince the people of Tau Cygni V that a place is just a place.
I have no idea what you're referring to about a trailer in a desert, but in actual Star Trek, everyone had a home, had food, had a place to live.
Regarding luxury apartments and vineyards, I must ask: why would you care? If you have a spacious and great apartment that meets your absolute every need for you and your family, why would you care if someone has more square meters or a higher floor on a high-rise? In a world where transporters and shuttlecraft and replicators exist, why would you care where your home is located except that it meets your personal vision of a perfect home? You can live in the middle of the alps and have every modern convenience at your fingertips and just enjoy the snow.
As for the vineyard, again, I think you're looking at this from a very current perspective; in a world with replicators and synthehol where only a few specific snobs care about real alcohol versus replicated alcohol, owning a vineyard and manually tending to it likely is just something where everyone goes "right, have fun with that." (Also, Picard didn't own the vineyard, his brother did. I guess in the Picard series he controlled it also? But never watched it)
I really cannot take the comment seriously as I think you both miss the point of the episodes regarding property/land and also are not considering how people might view apartment sizes and such in a world when transportation, knowledge, information, energy costs, food, basically everything is already taken care of. Remember, even humble Scotty thought he was being given an admiral's treatment in TNG when he got a _basic_ quarters for his stay.
Try to imagine that's what your normal life looks like, and then ask yourself how much you would care if someone has a few extra square meters.