[item2=Chirpyston] is a Steamworks Menagerie item from just this year; there aren't any in user shops. Is it intended that Quentin ask for this item?

It's possible one was recently sold in shops for 50k or less and that's why Q asked for it.

Quentin asks for holiday items... So yes it is common that he'd ask for it. Just buy from the menagerie.