In the battle with the Mad Janitor and even with the crowbar equipped I cant open the manhole, running on Mac and installed the most recent hot fix (0.9.11). 

It's completely RNG based even with the crowbar.  It took me two runs where i just spammed "open manhole with tool" before it actually worked.

Thanks for the info, will have another crack at it. 

I know this is a bit late, but I'll just add that I was only able to get it to work when I had the crowbar in my inventory, but not actually equipped. Not sure if I just got lucky or what.

Also useful intel, still have to reattempt the encounter but I now feel better equipped to handle the situation. Thanks chaps :D