I'm planning to draft an email to Holyday's office to request bike share stations at specific locations in ward 2, though I'm a bit perplexed as to how I should word it given his less-then-favourable stance on such initiatives...
I've never dealt w/Holyday.
But my 2 cents.
He doesn't want bike lanes, he probably doesn't care one way or the other about Bikeshare.
My instinct, appeal to his anti-bike lanes side.
Ask for stations along the Eglinton West Bike path, so you can connect to the Humber Trail, where there are existing docks at Scarlett and north at Lawrence.
You're telling him you'd like to bike recreationally, on trails, and stay off the damned road! LOL
Doesn't matter whether it's true, matters whether he believes you.
Stations/docks at each of Eglinton/Royal York and Eglinton/Islington is certainly a reasonable request and there's a good chance Bikeshare Toronto has 1 or 2 unallocated stations left (they did as of 2 weeks ago)
If the latter is true, it might not even mean spending any money. (right down his alley!)
Plus the City owns all the greenspace beside Eglinton, meaning it's no problem to find a spot, and no one's permission is required.
For the same reason, you'd like docks where the Humber Creek Trail runs between Islington, to the Westway and on to Royal York.
There you go, 5 docks, all on main streets, connected to the existing Bikeshare system; but appear to Holyday to avoid any need for bike lanes due to serving recreational trails.