If you haven't had a situation where you said "Damn, this would be a lot easier with radios", then you are probably throwing money at a problem that doesn't exist. Your buddies aren't going to want to get licensed or spend money. The end-of-days neighborhood watch thought process isn't going to work unless you are handing out radios, because nobody else is going to have a clue. If you have classes/training that require radios and they don't supply the class with commercial radios, they are breaking the law and you probably shouldn't hang out with them.
So anyway..
Here's what I do.
Howard Leights: $40-50, they work fine and have an Aux in
Peltors that fell off a truck: $30 ebay adapters convert the Peltor/MSA TP-120 (fat stubby) plug to 3.5mm headphones
Radios: Buy the nicest you are licensed to buy. Even the cheapest FRS radios have option ear buds or headsets.
PTTs: Not worth your time unless you are given/issued them for a work radio. Route your speaker mic on your non-shooting shoulder, then run a 3.5mm plug from that to your ear pro. If you don't want to use your electronic ear muffs, just run an ear bud under those. It won't mess with how the ear muffs work.
You use your speaker mic as a.. speaker mic, and you just run your audio to an ear bud or your ear muffs.
This is so you can visualize how the plugs work:
This is how you can route your cables from the back of your PC. I didn't route them under the elastic for this picture, but you can use rubber bands, the existing molle, or elastic shit on your PC.
Same concept with helmet mounted muffs. Cords are loose just to show the concept. My L shaped 3.5mm cord is missing in my bag, which makes it stick out of the ear muff a lot less.
Just remember.. only transmit what you are licensed for, and for what your radio is intended for.
The chinese radios are not legal to use with your other work radios, or on GMRS/FRS.