i think it's a great idea to have a radio station starting with localcasting the ga and then broadcasting via streaming and possibly a more powerful radio transmission. audio has the distinction over video and text as being a medium one can take in while engaged in other activities and i'm excited by what this can become.
that said, i would not support a $2,000 budget initially. i think better to demonstrably "solve" the open mic problem using minimal cost equipment and after that is working ask for funds to stream, archive, etc. specifically get it working in the square without sound boards, laptops, streaming, space, storage, etc.
have you looked at these transmitters:
my suggestion would be to get one transmitter, one wired mic, one shotgun mic (to pick up audience comments), and ask people to bring radios.
From: Danny Valdes <firstname.lastname@example.org>
Sent: Monday, October 24, 2011 3:01 PM
Subject: [GlobalRevolutionMedia] Re: Proposal from radio team
Hey media -
is a read-only link to the proposal that the radio crew worked on last
night. We're hoping to present this in full at your 6pm meeting today.
See you then!