I think it still is most important to make sure you can't carry the locked bike away. It's mostly tool-less homeless people roaming the streets at night looking for an opportunity imo. Only bikes I got stole were not locked to a pole because I forgot or assumed I would be back in a minute and wasn't.

I agree about the shitty-ness, it is less likely to attract attention and you feel less bad leaving it out on the streets but I think most people would prefer to ride a nicer bike if only people with keep their hands off your property.