The concern I have (in NYC FWIW) is that someone will see they can’t steal the bike and will instead just trash the thing while it’s still locked. Maybe I’m too pessimistic.
That's pretty much my experience in the city where I used to live. I'd regularly pass bikes securly locked to some post or other but with the front wheel stoved in and bent. I always assumed a would-be thief had done it in a fit of pique, after failing to get the lock open.
Drunk assholes smash random stuff all the time without first trying to steal it.
Bicycle wheels are unfortunately easily bent by kicks from the side.
These days it seems worth it to get a folding bike. I am currently trying to get one myself so I don't have to worry about it getting stolen OR trashed. I just fold it up and take it inside where nobody will touch it