We are seeing the obsolescence of Legacy addresses. Maybe they will be rare someday and not generated by most new software.
Since there's literally no advantage of using it over SegWit, I don't see why not.
Yeah, but they're so cute! Lol. I remember reading really old threads here, and vanity addresses used to be a pretty big thing--I don't know if they still are, but it'd be pretty damn hard to create anything cool out of a segwit address unless maybe it starts with a 3.
On a related note, if you import a Mycelium seed phrase into Electrum, you have to choose BIP38 and then you get a choice of address types, legacy included. That confused the hell out of me back when I was much more ignorant about these things (I'm still ignorant, but less so because of the collective wisdom of bitcointalk experts).