In reply to:

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Although it's possible, it would be highly unlikely. The FCC is a government agency, it's doubtfull you could call and talk to a real person in an 8 hour period - say nothing about getting them to leave their warm office and going out in the field to work.

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Plus the fact that someone has to call and complain first. The FCC doesn't monitor all the frequencies all the time especially since the decline of the Amateur Radio and CB hobbies. And if he's using a frequency nowhere near a broadcaster's and he's in a somewhat remote area I wouldn't think he'd have to worry.

I think it's a great idea.
I was thinking of something like this myself for my shop. Since allot of the equipment I use is very noisy plus the fact of when I have to go into another part of the building and can't hear my Empeg an FM transmitter with a little bit of power would be great. I could get a cheapy walkman style radio and a single ear bud so I can still hear other people.