TAS, Season 1: "The Survivor", because of the "billionaire philanthropist" in an economy supposedly without money. I don't like when people keep contradicting themselves. Plus it's just a cartoon, it hardly compares with an episode of another series unless the latter is really bad.
TOS, Season 1: "Where No Man Has Gone Before"
TNG, Season 3: "The Survivors"
TNG, Season 2: "The Emissary"
DS9, Season 1: "Emissary"
TNG Feature: "Star Trek: First Contact"
DS9, Season 1: "Past Prologue"
As opposed to Flint, who bought an entire planet? Or the miners hoping to strike it rich in "Devil in The Dark" or "Mudd's Women?" Or all the various merchants, traders, mail-order brides, and con artists we saw on TOS?
The whole "no-money" business is more of a TNG thing and never really applied to the Final Frontier of the 23rd century, where things were much more rough and tumble. "You've earned your paycheck this week, Scotty."
Greg Cox is right.
Curiously I have heard of a citizen of the USSR who became a millionaire inventor, and didn't Erno Rubik in Communist Hungary become rich from Rubik's cube? Isn't there a lot of trade between Communist China and capitalistic countries? Wouldn't it be possible for a Communist Chinese naval vessel to rescue an American billionaire from an island where his private jet crashed?
TOS and TAS are full of references to money, wealth, poverty, salaries, etc., so either a money less Earth and/or Federation is part of a larger interstellar culture with private enterprise and money in many of the known planets and cultures, or else Earth and/or the Federation themselves have free enterprise, capitalism, and money.
Even though Lincoln said that a house divided against itself cannot stand, the USA did stand with both free states and slave states for about 71 years, and continued to stand with both free states and tyrannical oppressive states for about another century until the civil rights era.
The Holy Roman Empire contained states, the Imperial Free Cities, that were republics (usually more oligarchical than democratic), states ruled by religious leaders, and states ruled by hereditary nobles, as well as self governing peasant communities, etc. The Holy Roman Empire had a Jewish minority, and after 1648 three legally protected Christian denominations, although most individual states had state religions.
The Empire of India or British Raj had many provinces ruled by the central government, and also hundreds of native states ruled by hereditary nobles, kings, and higher ranking rulers.
So the idea that in some or all eras the Federation might be contain money less societies and also contain societies with free enterprise, capitalism, and money seems plausible to me.
Even in the era of TNG, when Earth and/or the Federation have no free enterprise, capitalism, or money, other advanced societies that they deal with do have them. So a mixed interstellar civilization is perfectly possible in the era of TOS, whether the Federation itself is money using, money less, or mixed.
As far as I remember, the earliest references to a money less future are in
Star Trek IV: The Voyage Home:
[San Francisco - downtown]
CAR DRIVER: Why don't you watch were you're going, dumb ass!
KIRK: Double dumb ass on you!
McCOY: It's a miracle these people ever got out of the twentieth century.
KIRK: They're still using money. We've got to find some.
KIRK: Spock! The rest of you stay here. ...The rest of you break up. You look like a cadet review.
[Antique store]
ANTIQUE STORE OWNER: Yes, they're eighteenth century American, quite valuable. Are you sure you want to part with them?
KIRK: How much will you give me for them?
SPOCK: Excuse me, weren't those a birthday present from Doctor McCoy?
KIRK: And they will be again, that's the beauty of it. How much?
ANTIQUE STORE OWNER: Well, they'd be worth more if the lenses were intact. I'll give you one hundred dollars.
KIRK: Is that a lot?
[San Francisco - downtown]
KIRK: That's all there is. Don't splurge. All set? Good hunting. ...Well, Spock, here we are
And:
KIRK: Noon tomorrow!
GILLIAN: Are we leaving?
KIRK: Come on! We don't have much time.
GILLIAN: Uh, ...could we have that to go, please?
WAITER: Sure! Who gets the bad news?
GILLIAN: Don't' tell me they don't use money in the twenty-third century.
KIRK: Well, they don't.
So some people may believe that is evidence that between TOS and TAS and
Star Trek IV: The Voyage Home there was a great social change and revolution and that Earth and/or the Federation no longer has private enterprise, capitalism, and money.
And other people may believe that is evidence that between TOS and TAS and
Star Trek IV: The Voyage Home there was a great but much lesser social change and revolution and that Earth and/or the Federation still has private enterprise, capitalism, and money, but money in the form of bills and coins has been abolished, all transactions being by credit card and/or electronic money transfer. These people believe that when Kirk & co. talk about "money" in
Star Trek IV: The Voyage Home they are referring to physical forms of money, cash and coins. These people believe that the really big social social change and revolution that more or less ends free enterprise, capitalism, and money on Earth and/or the entire Federation happens after the era of
Star Trek IV: The Voyage Home and before the era of TNG.
And even in the era of TNG some highly advanced societies with interstellar travel still use some forms of free enterprise, capitalism, and money. So there is absolutely nothing to prevent members of a money less society from meeting a famous billionaire philanthropist.