In article rs.com, O:P\)
says...

As for sailing/boating schools, any suggestions?

Others have responded intelligently and in more detail than I have to offer for
your other questions.

I would strongly URGE you to take a course or two, and perhaps join a club for a
year to see what you like.

In Toronto, there are many clubs and groups that offer either or both power or
sail lessons.

http://www.sailing.humberc.on.ca/
My personal favorite, I have both taken courses from them, and then belonged to
their sail club for a couple of years. Best yet, courses taken are tax
deductable.

http://www.queensquayyachting.com/
These guys are downtown, in the inner harbour. More traffic to worry about, but
perhaps more convenient location.

sdg