I am generally using topdown tokens in VTTs, because they are not only accurate when seen on a battlemap, but also quite easily available those days, and some of them are absolutely gorgeous (my favorites ones, those from Greg Bruni and Devin Night for exemple).
I have been playing with the attachment tool in Owlbear Rodeo since its beta release.
One of the use I have experimented is one I had used in Maptool in the past (with portraits as states, as there is no attachment in Maptool).
Not sure if I'll use this frequently because I am mostly a topdown tokens GM, but maybe if I need to prepare a game in a pinch.
For the record, I imagined this because I need tokens that show orientation (I don't play D&D and derivatives) and because I hate when portraits tokens are jumbled with faces in any orientation.
