I tried this a bunch of years back, though across the river in Jersey City. I moved to a building that was an enclave of sorts that had zero street parking. You could of course pay for the garage to the tune of ~150 a month at the time. I had a motorcycle, and realized that I could park it across the street from my office building a few blocks away, and a ticket for street cleaning was $20. They would ticket me every other week, so $40/month in total. I guess someone got sick of my shenanigans despite me paying the tickets off promptly each time I received one, and one day my bike was taken to bike jail. Maybe some tickets blew off, but I think they were just done with me, and it cost me $500 to get it back. I sold the bike shortly after, I had acquired a serious girlfriend, and was using it for trips home and to the beach (both about 30 miles away), and there was no way I was going to make her sit on the back of a crotch rocket that long.

However, I did pull a similar stunt in lower Manhattan for awhile too, though I moved my bike on street cleaning days- though to another illegal spot by my office building- at that point I was living in Battery Park and my office was right off the west side highway in Tribeca, and I never had a single issue doing that.