I understand what you are trying to do, and i really have no clue what the legal issues may or may not be. If you have say a GMRS license and you want to take your scanner feed and run it through a low power gmrs radio i don't know if that constitutes illegal use or not. The only constraint i could see is using a UHF radio with a VOX( voice activated transmit feature). You can then run a plug out of your headphone or ext. speaker from your scanner into the mic in on your radio. I'm not sure which would make for clearer audio, the headphone or the ext. speaker. From experience setting up my online scanner feed, getting the audio clear is a trial and error system.
I had thought about something like this in the past, just from a "could i do this and make it work" standpoint, but i never found a need for anything like this. I could see it being useful if you had a very good base setup with a high tower and good antenna that were picking up broadcasts that a handheld scanner couldn't. It that case you could just program your scanner for the gmrs frequency and you would be in business.
Good luck in your search for answers