This quote is almost useless unless you know its origins. I think it comes across as a bit disrespectful of the people you're aiming it at because most won't know what the hell you're getting at unless they look it up.

I'm going to have to respectfully disagree with you there. If you're having to research the history of the phrase, you're overthinking it. It means exactly what it states, no tricks. "Free speech" is a well known phrase that means the unencumbered ability to say what you like. "Free beer" means something that everyone (ostensibly) likes being handed out without the need for payment. I'm not sure how one could more simply explain the "free" dichotomy. If you've got a suggestion, I'm open to hearing it.

I felt stupid for the longest time with this phrase. Even after looking it up. Until I knew the history more I didn’t get it.

The confusion comes from the fact that beer generally isn’t, well, free!

There is no implication in the quote that beer is generally free, just that "free" in the context of beer generally means gratis whereas in the context of speech it does not.

Where do you live that beer is generally free? I want to go to there!

If you release a game "free" as in "free speech", how is it not "free" as in "free beer" as well? What would prevent people from redistributing it? Nothing.

I guess I don't understand the question. Plenty of open-source projects charge money for a license. And even closed-source / non-free games have pirates. The availability of the soucre code does not determine a business model, the licensing does.

It's not really the end of the world if only some people pay for your software. You could charge for binaries but let people build from the source. You are willingly giving people the freedom to redistribute those binaries, such as to their friends. It's just not an issue. It's not a crime that needs to be prevented.