IMHO, a cashless economy doesn’t necessarily prevent one from working or owning a business. I could see land/housing being doled out by the Federation by application. Assuming the spot you want is open and available, you fill out the forms explaining what you want and why, and it goes to a comittee for approval. If more than one person wants the same land, there would be hearings and each claimant would make their case.
For restaurants, well, I know a lot of people (myself included) that have a little dream of owning a restaurant, but would find the expenses and risk too much. But in a universe with replicators, robots, and high levels of technology, everyone who wants this dream can have it. Why would I go to someone else’s restaurant when I can replicate it at home? Well, people like to go out and eat, and for some its more than just the food, its the whole experience. Plus, without any expenses or costs, the only limit would be your imagination. You could come up with all kinds of different combinations. Always dreamed of a Mexican/Korean fusion restaurant, or wanted to combine elements of Russian and Indian cooking? Use your replicator to replenish your ingredients and experiment your heart out. When you think you’ve found something good, put it on the menu. I could also see some taking pride in just replicating ingredients and always cooking and preparing the food themselves rather than just replicating a finished dish.
I always assumed anyone with a restaurant anyone would want to go to, wouldn’t replicate anything (people are snobby and insist they can tell) and real ingredients would be pricy.
I marathoned DS9, so I’m fuzzy on the details, but I swear I remember someone (the Bajorans?) bitching about how "Yeah, it’s super-spiffy to be in a post scarcity economy if you’re on Earth or Vulcan or anywhere at the center of the Federation, but for everyone else out in the suburbs or the “rural” areas, there simply aren’t enough replicators to go around and that’s why there’s money on the frontier while the people in the core of the Federation are living in an Oz-like fantasy.
The plot involved something about a mega-replicator that was used for terraforming planets, if that helps.
I thought that was an extremely elegant solution to about 90% of the magical cash-less society that everyone on Next Gen blathered about, despite A) poker being played, B) everyone regularly talking about money, C) con men, etc and D) limited resources (land, labor, gold-pressed latinum(?), dilithium (which can’t be replicated, IIRC). It still doesn’t solve the problem of what turned the people of the Federation into non-humans (Humans are competitive, and the weird quasi-communism of Next Gen makes no sense–“I find cleaning toilets fulfilling, so I’ll do it even though I could live like a king and not”)
There’s also a speech by Quark in DS9 about how it’s easy for the 1%ers in the Federation to sneer at Capitalism now that they have magic-tech, but for the hoi-polli who don’t, it’s kinda necessary. It was one of his best moments.
You’re assuming replicators are 100% efficient, which they obviously aren’t. They can’t even produce ersatz chocolate beans that pass muster. By extrapolation, I find it hard to believe any other dish would be equal (or superior) to one made from scratch with natural ingredients.
Nog used all his transporter allowance to eat cajun. I have seen them use barter for most transactions like mssmith said in 2008. How many tribbles was it for a few strong drinks? They probably limit the number of beach bums by some sort of reward system.