Seems like you are being sarcastic, but yes, if you play loud enough and to a big enough audience you do indeed owe royalties. In fact bars and restaurants are required to pay for this exact reason.

My goal is that musicians get fairly paid for their work as opposed to making sure I am following every subtle licensing technicality in my own home, which is only an exercise in pedantry and accomplishes nothing practical for musicians.

I don't talk with the attorneys who create these complex licensing rules at Amazon, iTunes, etc. I talk to musicians. None of whom have ever had a problem with listening to their music with a small group of friends or family. The problem is with a platform that allows me to fire up a server and then invite thousands or millions of people to listen to someone's music for free.

Do you remember CDs, cassettes, records, etc.? Is it illegal to let family listen to those?

Without even looking at the law I'm going to guess there's some kind of clause about "within reason". As in, you can't reasonably claim that all 350,000 people who've downloaded the music you uploaded can be classified as "friends". That would certainly fall under broadcast or distribution licensing and legal terms.