Always DHs always on Tue, Fri, and Sat? Or sometimes single games on those days?
Could we always have double headers on Tuesdays and Fridays/Saturdays can be double header or single games...
Should the Fri & Sat matchups be against the same teams (and Tue games against different teams)?
Yes!!! perfect....
When on the calendar should the season start? When should it end?
The league is based off the coast of eastern canada/usa so games should be August-September with the championship game (best of three) ending before October starts (too cold! 
)....
A 1-division league will not be able to have an All-Star Game. Two divisions of three games would allow for it, but that may give a playoffs setup you would not want. Anyway, if there was an All-Star Game, when during the season should it be?
Understand....no all-star game, that is OK......
gmo - thanks you are the best!!!!!