He also has a neat little interaction with the son of Brimmer's favorite employee in "Death Lends a Hand." Leo's wife actually DOES run up, angry and scared about this strange man in a raincoat pushing her son on the swing.
You can definitely see that it was a different time, though. As Cassa noted, his playfulness with the girls in "Identity Crisis"--especially telling them both that they are pretty--would upset some people today.
RE: the Bye Bye Sky High IQ case, I also wonder what Caroline Treynor's parents would think in 2006 if she went home from the Sigma Club and told her parents that the police lieutenant told her he liked her for her body instead of her mind.
Columbo also touches girls and women more than would be acceptable today--e.g., laying his hand over Joanne Nichols's clavicle before he leaves, while she is dressed in a robe. I imagine some young college women would find that gesture a little disconcerting from a police officer they just met.