So, maybe common knowledge now, but the inevitable death curve was supposed to be there to teach you about the evils of capitalism. It's not supposed to be a fun game.
Playing Monopoly with my [parent] made me so terrified of sucking at board-games I avoided anything of similar complexity for literally ~3 decades (with the occasional exception because the unrelated person convincing me to give them a go was a very good ''kisser'' and didn't get mad when I didn't play correctly or optimally), I even avoided this stream when it was live, and the vod for THIS long.
I haven't watched the whole video, so chat might have pointed this out, but it isn't the "Reeding" Railroad; it's the "Redding" Railroad, pronounced like bed or dead.
It warms my heart greatly that they not only choose to play monopoly but play by standard rules only. (I also remember the days of 5 1s, 5s, 10s; 6 20s; 2 50s, 100s, and 500s.)
There's also Cheaters edition monopoly, that says if you can get away with it it is a legal move. if you're caught, reverse that move and put the handcuff on until someone else is caught.
I think the problem with monopoly even with the correct rules is it still maintains too much of its roots ... ie a showcase about why monopoly power is bad. And thus its a game where you agonizingly slowly are bleed of money till you are finally out of the game, while it's fairly clear from a long time out that you can't win and the person bleeding you will win. Then when you are out you have to sit and watch the others play which can often be an extremely long time.