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 ...

Maybe getting rights to use one of these guys would be cheaper, the Dude didn't strike me as a brand snob:
Kapali Coffee LiqueurKamora Coffee Liqueur

I had this poster up in my college dorm room after scoring it from the free bin at the video store back in '99 soon after Lebowski came out on VHS (an instant grab for me since I was one of the few that enjoyed it in the theater), and for years after it followed me around the country to various cities and states. So generic though it may appear, the title font at the top there will always be the "The Big Lebowski" font to me.

The Big Lebowski poster

Also if we're going with the theory that "the money" is a central theme of the film and therefore a "$" is justified, shouldn't the final "i" be rendered as a toe (or a joint, for that matter)?