No money is NOT on the worst list by any means!
Step out of the "in-universe" for a moment, and look at it from a story telling point of view. Having money in the story, with all the things that come with that, adds a level of complexity to the life's of the characters that otherwise would be absent.
Having no money would be simplistic and easy. It'd be like having a planet with one climate (desert, forest, ice). One race. One culture. One religion. One style of dress. "In-universe," (out of range of the cameras) the worlds visited likely aren't the same everywhere, they're complex and diverse
So "in-universe" the bolt of cloth did come out of Beverly's pay, and the poker games did have monetary gambling, the O'Brien's wedding gift from the replicator was deducted from Worf's account. And when you get food and drink in Ten Forward, you do pay for it.
Tell you what, let us cut this down to a basic fact of the show ... WE SEE AND HEAR THEM USING MONEY.
Take for example the house we see Kirk in (Generations). Kirk clearly states that he owned the house, and he sold the house at some point. While there is some debate, the usual interpretation is that the time period where Kirk is cooking the eggs is between TMP and TWOK. So prior to the events of TVH, Kirk owned a piece of real estate, that he would sell.
Scotty bought a boat, Uhura tried to buy a tribble.
This is one of the quotes I usually add to debates on this subject. The writers of the show lived in a society with a market economy, this is why (despite Roddenberry's wish) money and monetary reference keep making their way into the episodes. It's how for instants a Federation member got a major bank. And Quark was able to sell his shuttle in Earth's system for scrap. And a corporation within the Federation was able to own entire planets.