How big are the blocks?
An actual measurement would be helpful and is it line of sight to the speakers?
Rough total distance for the line is about 1500 feet. Longest distance from transmission point would be just under 1000 feet.
The 'previous' solution that was used for music along the street was in ground 'rock' speakers in planters. It worked, but road reconstruction has broken that solution. They don't have the ability to re-cable that, so now we're trying to come up with a wireless solution.
Battery operated isn't 100% required for this setup, but for flexibility, and being able to use the system for other possible events, battery operation would be super convenient.
Some latency isn't that big of a deal, since the speakers are going to be at relatively low volume and spread far enough apart. Think more background music than focused rock concert levels. We're actually looking now at an IP based solution that would let us either run over a WIFI network or even over the internet to get the job done.
This is one of those case scenarios where it would be REALLY awesome if the FCC would make a couple of frequencies available in the FM band that could be licensed for temporary use.