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I felt geeky so made a quick spreadsheet of remaining Cascadia Cup possible results.

Remaining Cascadia Games

Timbers Highlights

2/3rds of outcomes have the Timbers winning outright and 1/9 outcomes have the Timbers making it to a tiebreaker if they beat the Whitecaps on 9/28.
7/10 of Timbers wins/draws involving Timbers exist in a scenario where Timbers beat Whitecaps on 9/28. 1/3rd of outcomes, based on current tiebreakers, are favorable to the Timbers if they draw Whitecaps on 9/28.
2 outcomes (~7%) are Timbers-involved draw. As of now, the 6th tiebreaker criterion, greater number of goals in all cup matches, would apply in any Timbers-involved draw (+1 GD and 6 GF between Vancouver/Timbers, all three teams are tied at +9 GD in regular season). Timbers currently wins on tiebreaker in both of its potential draws; at this point, it would bring Timbers-favorable outcomes to 37.01% of all outcomes.
Timbers cannot lose to the Whitecaps on 9/28 in order to stay in Cascadia Cup.
If Timbers win 9/28 and Whitecaps draw Sounders, the Timbers win the Cup regardless of their 10/19 result.
Both of the Timbers remaining Cascadia games are away. Last 5 away games (Leagues Cup not included): W-D-W-L-L, Away PPG: 0.92, ranked 20/29 for away games in the league

Best route to guaranteed win: Timbers win v. Whitecaps, Whitecaps/Sounders draw

Over 50% of outcomes result in an outright Whitecaps win.
If Whitecaps beat the Timbers on 9/28, they will either win outright or move into a draw with the Sounders, where they currently lead on tiebreakers.
If Whitecaps draw Timbers and beat or draw Sounders, they automatically win the Cup.
Both of the Whitecaps' remaining games are at home. Last 5 home games: L-W-W-W-L, Home PPG: 1.55, ranked 21/29 for home games in the league, 82% of home games result in both teams scoring at least once.
All potential draw scenarios involve the Whitecaps; the Whitecaps currently beat Sounders but lose to Timbers on tiebreakers

Best route to guaranteed win: Whitecaps win v. Timbers, Sounders do not win v. Whitecaps

Sounders can only win outright if the Whitecaps do not win on 9/28 and the Sounders win 6 points over their next two games against Van/Por. Only 2 outcomes (~7%) have Sounders winning outright.
The number of outcomes the Sounders can win outright is equal to the number of outcomes the Sounders ends up drawing in match points. There are more scenarios available for a draw than for a Sounders outright win on MP.
Sounders currently lose every scenario that goes to tiebreakers. However, if the next three match fixtures are Whitecaps/Sounders/Sounders resulting in a draw on points, the GD is erased if Whitecaps only beat Timbers by 1, and the Sounders score +2 over Whitecaps, or +1 over Whitecaps and +2 over Timbers.

Best scenario: Whitecaps do not win v. Timbers, Sounders wins v. Whitecaps, Sounders wins v. Timbers