Afraid I don't have the time for a comprehensive reply, so try
http://www.tobma.com or attend the next meeting which is Nov 14 at 25 Cecil St or you can meet some of the same people at the next CMWC meeting Oct 25 @ CBN 761 Queen W
your last question is a quick answer, as a foot or bicycle messenger you're WSIB covered by special provision, it's automatic you don't have to do anything to activate coverage