CTBuckKilla,

The 500 ft zone only applies to firearms hunting. You can be as close to a building as you want with a bow. You can also be closer than 500 feet to a building, hunting with a firearm, as long as you have the written permission of the dwelling's owner. EDIT: I no longer see this statement listed in the guide, this may no longer we an allowable option for anyone other than a landowner...

http://www.ct.gov/dep/cwp/view.asp?a=2700&q=323400&depNav_GID=1633#T OP

The first portion of your argument is valid, even bowhunters cannot fire across a road or towards an animal or an occupied space. This matter will probably be jointly decided by the city and the DEP, due to the overpopulation in that area. If memory serves me correctly, the last deer population study had Milford at #1 or #2 in the state, in regards to deer per square mile. Factor in the large human population, the wealth of the population, and the insurance industry---naw, I don't think these suggested restrictions will pass...

PS> I'm a Certified CT DEP junior Bowhunting instructor, but unfortunately I have moved out of state, and hence won't get the chance to teach Bowhunting Safety to anyone in the state...