I have kind of the same problem @Boshea keeping the models together that need to be together, while trying to compete through the terrain and for the schemes makes my brain hurt lol I keep forgettting stuff! Last game I totally spaced that Lenny could heal himself. I would have probably lost anyway, but my opponent had obviously chosen assassinate as their scheme and I parked a slophauler next to Lenny to try to help with that but ultimately lost him.
I can't offer too much advice on the issue, the only thing I have figured out after like three more games than you, is to make notes of how the combos go - so maybe, just maybe, I'll remember lol I'm sure a lot comes with practice too.
your second list is close to what I want to run as well! except I'll take Lenny where you have Trixie (Don't have her yet). And don't forget Masters get 3 upgrades and you can give Sammy 2 as well (I believe that's true of all henchmen but you might want to look it up), plus henchmen can use soulstones... something else I forgot in my last game sigh
Also - someone correct me if I'm wrong please! but is it a good idea, using Somer as a summoner, to take three Bayou Gremlins so he can hopefully get off Git Yer Bro 3X for summoning more? I've been taking 4 to start but maybe that's not the best use of the points