So radios sort of range between $40 (Boafeng) and $110 (Wouxun).
Headsets, you can start with a Pryme surveillance two-wire system for about $100 - $120 and go up from there. I know these and other quality, but lower cost brands are available at Norquip in Burnaby, which is a store I recommend. Email them, ask for Andrew, tell him that Lindsay sent you. Also, add the mouldable earpiece for $10?, it's totally worth it. Saves your ear from getting raw. They are sized thought (small, medium, large), so you'll have to guess your size.
After that, it's up towards MSA, Honeywell, Tea, etc, for higher end comms.
http://www.pryme.com/index.php?l=product_detail&p=2395
I just picked up a Weather proof speaker mic by Stone Mountain and an clarity enhanced earpiece by Impact from Norquip.