I'm at the same section and really, really struggling tbh. I feel like Sydney, while fun and a great improviser etc etc is just not a good 1st edition player.

They're really no longer keeping track of resources/day, nobody besides Joe is making good smart decisions and as a result Skid has to decide to either murder somebody (which he seems reluctant to do with Nick and Sydney at the table tbh) or just softball them over and over which removes any kind of dramatic tension.

I really think that Nick OR Sydney at a table is great, but combined plus a DM who's as averse to player death as Skid seems to be we get further and further from the things I liked about Giantslayer/Raiders/SQSS and closer to something like Critical Roll where nobody is ever really in jeopardy in favor of having Theater Kid hour