- I think separating the players on the left, with a blank line or horizontal bar, would make that area a lot more readable.
- If color is an option, I'd make Thugs blue and Holdings green.
- Lamonte's said "fewest," should be "most."
My first approach for the AI would be, for each decision, consider each option, for each option consider each order it could play out its cards, and simulate the rest of the game, with it playing the cards in that order, on-the-table things happening, but no card plays from other players or further drafts. Pick the option that wins by the most or loses by the least. Card-drawing cards would want to assume certain below-average draws (cards not in the deck that are just used for this). So overall it could plan a little, and recognize how some things matter, while trying to make meaningful plays. In my game they never stopped Jenny's from working, and one player gave up Insurance Office to play Tommy's; those kinds of things would be fixed.
After that you could have a pick order for turn one, modified by what else is in the hand, and you could use the pick order for turn two in the cases where the first pick is also a good turn one play. This would address the lack of ability the previous algorithm has for planning on turns 1-2.