Love the use of Playwright for the contest intel...I am currently using Playwright to redo some prior scraping projects and seeing real world examples such as these is a big help.
You attack the problem like blackjack card-counter would. You assess the rules, make mathematical odds projections when possible and logical ones when not, and keep a keen eye on what you are up against as to judge how to best attack the money.
Thanks for the smart write-up...its been a big inspiration for me.