PCYC (Port Credit Yacht Club) has excellent racing and a lovely (small - about 18 boats) who live aboard year-round. They have their own Yard and workshop for members' use. They are also close to the GO Train into Toronto.
They made a push a couple of years ago to increase acceptance of members with boats 35' or less (their bigger slips are all taken, apparently) by giving them a break on entry fees
... don't know if that's still the case.
I'm not affiliated w PCYC in any way (although I do know their Race
Director), just know this because I looked into it myself a couple of years ago.
Good luck in your search!