You are going to want to know ways to bypass the 400 on a friday, your commute to markham "should" only take 40 min give or take depending on how you drive. I work out of innisfil and have to drive between barrie and toronto rather frequently.
As for the boat ask 10 guys get 10 answears.
I just bought a 20 ft chaparral off my buddy and i love it, however on a rough day it doesnt do me any good on simcoe.
Good luck with your new home and hopefully we see some good simcoe reports!