I think there's two ways to look at this: the way I'd like it to be and the way Roddenberry thought it should be.
The way I'd like it to be is: of course they don't use currency. What we think of as currency has changed dramatically in just the 20th century and will no doubt change again. I can imagine a future in which I rarely, if ever, carry physical currency. In fact, with my ATM card, having cash on my person is fairly rare.
So in ST4, when Kirk says they don't use money in the 23rd century, I'd like to think he's talking about currency.
However, what Roddenberry portrayed (with increasing strength as he got older) was a small-c communist utopia. There's really no other way to put it. Just look at what we saw:
Humans have literally evolved beyond the need for material wealth. This is stated repeatedly, and in the context of a civilization with food processors and later replicators, it actually makes sense. Most of what we do with our lives ultimately involves food, clothing, and shelter. If you could cheaply replicate basic needs, everything else is just gravy.
(Just imagine Treknology applied to building homes, for example. Want a house? Just replicate one. It couldn't possibly cost very much, thereby eliminating the single largest debt held by any family in America.)
A wise, omnipotent central government sees to the needs of every individual. We saw that over and over. The Federation is everything, makes most of the big calls, and rarely screws up.
We are led to infer that even in a galactic government, the activities of every individual are closely monitored. There is no Federation citizen about whom the various crews of the franchise cannot obtain instantaneous, detailed information. In fact, the same is often true of members of major non-Federation aliens.
Weapons ownership is tightly controlled. In almost every instance, only government operatives are allowed the right of self-defense. In 24th-century-era Star Trek, individuals’ weapons are removed automatically by transporter before they can even materialize.
Capitalism is portrayed as either evil or ridiculous, particularly as embodied by the Ferengi.
In short, it's all consistent with the kind of small-c communist world that Roddenberry fervently believed in.
I think the ultimate answer to this question is: like it or not, Roddenberry's Star Trek is a small-c communist utopia. The only time it's not been portrayed as such is when Roddenberry wasn't involved or when he was otherwise occupied and couldn't control it.
As an example: Roddenberry hated "The Trouble With Tribbles". But he was on vacation in and around the time it was produced, leaving the producing chores to Gene Coon. It was Coon who liked "Tribbles," not Roddenberry.
You'll also note that "Tribbles" is one of the few episodes that actually portrays capitalism -- albeit to comedic effect. I'm certain this would have been changed had Roddenberry not been in Hawaii at the time.
The third season (and "Requiem" is one of these) had no Roddenberry at the helm at all. Consequently, things like "wealthy financier" and buying planets could get past the communist filter that was Roddenberry.
Dakota Smith