I agree that the "$", and the new font that comes along with it, looks bad.
Some discussion starts in another thread here:
https://pinside.com/pinball/forum/topic/tbl-playfield-layoutmy-thoughts/page/8#post-1764774
The suggestion is raised in that thread that DP is required to use the official Lebowski font (including the "$") under their licensing agreement. So perhaps what we're seeing is the new, official, (and far inferior) font for TBL. But if they're required to use it to get the license, not much DP can do about it ...