Mostly smooth execution, RNG could have been better in places though. (Needlessly driving to the station before waiting for Taselli also cost me some time; and I miszipped at the office a few times.) Sub-20 is definitely possible with god RNG, but I don't currently feel inclined to grind for that...
Regarding poker: I throw away $601 before the game starts to get my balance closer to $0, intentionally lose the first game (which immediately kicks me out of the table), hit F4 to rejoin the game right away, intentionally lose the second game in such a way that my balance goes below $0 and loops around (which the game counts as a win), go get the bug from Detective Angland, and then give all my money to Woody so I can "win" by going below $0 again in the third poker game. I could go below $0 in the first game (which is the 100% strategy), but that would actually lose time in Any%, because I'd have to spend almost a minute waiting for the back-up team to show at the hotel. For some obscure reason, the game was coded so that the back-up team is already there if you've both lost and won at poker exactly once. (This is not a new strategy; FractalFusion's run already used it.)
Played in DOSBox 0.74, maximum cycles, Tandy emulation (which prevents me from using "pr24" instead of "nightstick"). Stream VOD: