OP:

I would start cycling to work and then ask for forgiveness/accommodations.

It seems like any company (whatever industry it is) has people that constantly ask for all sorts of (what seems to management) pie in the sky accommodations and then once delivered, those asking fail to use them. It's a waste of management and company resources.

On the flip side, if you start biking to work daily, find a secure and discreet place to park & lock your bike (under a stairwell may work) you have some leverage to show management that providing accommodations may be a viable option. If they say no, then just continue riding and parking where you have created a spot.