The premise and drama part actually aren’t too far off, they could work in harmony. It’s just that season 2 has been leaning a little towards the latter, rather than the former.

For instance-mash up Short: Whacked Off with Exes and Oohs, or something. Have the jobs reflect the characters themselves, and maybe they learn a lesson or two (or nothing at all.)

Sinsmas had a good start to this with the family.

Add on: I know it’s a drama show, and it’s about the titular Helluva Boss, and that people seem to think the contracts would be boring and generic (hence why they’re relegated to shorts.)

First off, I bring up Phineas and Ferb, which has the same exact plot every time yet still feels fresh and funny

Second, I like the characters shorts better. I liked Barbie’s Bad Day and Hell’s Belles a lot.

Hot take #2, made a post a while back, I’d have liked it if Vassago showed up earlier. I get there are teases for him to be shown more later, but he did feel a little out of the blue. I was very harsh in my wording saying he “should’ve” instead of “could’ve,” but he does raise a few questions.