At what point to do you need some sort of license for a radio? I know there limits as to how much you can boost, but since my generation had gotten their hands on cellphones rather quickly, I never really had a need for them?
It's because the radios aren't worth a crap. Put one on a spectrum analyzer, key the mic, and watch it throw RF all over the place.
For a halfway decent dualband analog rig, I'd spring for the Yaesu FT-60R. They're coming in new at about $150 right now. Solid performance and well supported.
At what point to do you need some sort of license for a radio? I know there limits as to how much you can boost, but since my generation had gotten their hands on cellphones rather quickly, I never really had a need for them?
The general answer is: Any time you want to utilize a service other than CB, MURS, Marine Radio, or FRS. You're usually good to go with the bubble-pack radios you find in nearly every retail store. Much beyond that, and you need a license.