Leave the widowmakers. The angle is too steep to undercut and hope for a fall. If what they're leaning on is dead you can take down both at once but that's a tree fellers no no.
I think the most I ever paid was around $1,700 bucks. $25 tickets turned into 75 dollar tickets after the late fees and demand charges. 350 sounds about right for boot removal.
I'm with hubb on this one. You were fortunate previously but it's not by right. Speaking as someone who lived most of their life in Boston and has had multiple boots put on their car