Parallel Dream-Eaters Run with Parallel "Skids" O'Toole

Notes

Since the release of the Parallel "Skids" O'Toole, I thought it'd be fun to do a Dream-Eaters run (Parallel campaign with a Parallel investigator) with him.
Would have loved to pair him with Parallel Daisy Walker, but I'm already running her in another campaign

Overall, Parallel "Skids" O'Toole was immensely fun to play with.
His special allows you to trigger all sorts of Rogue tricks such as Momentum (1), Double or Nothing, Quick Thinking, and All In (5) with minimal risk.
Eucatastrophe (3) combined with his ability also allows you to quickly reuse the aforementioned tricks.

I initially ran him with Mauser C96, and later with .41 Derringer - but I found his meager 3 made it too inconsistent to rely on. .45 Thompson was a far more reliable choice early game - though that meant I had to sacrifice Lockpicks (1) moving forward. Relying on 2x Backpack as a backup in case I don't draw guns early was also sufficient given the small deck size for Parallel "Skids" O'Toole

Alternate build

Should probably squeeze in 2x Manual Dexterity for Lone Wolf and Daring Maneuver

Upgrades

High Priority:
Chicago Typewriter (4) for .45 Thompson
Momentum (1)
Sharpshooter (3)
Delilah O'Rourke (3)
Medium Priority:
Sure Gamble (3)
Eucatastrophe (3)
Lucky Cigarette Case (3) not yet available on arkhamdb.com

The Dream-Eaters Campaign Spoiler Warning

The Dream-Eaters (The Web of Dreams) Campaign Log

Two-handed solo The Dream-Eaters campaign (standard difficulty, taboo Sep-2019)
The Dream-Quest with Diana Stanley and Sefina Rousseau
The Web of Dreams with Minh Thi Phan and Parallel "Skids" O'Toole
Scenario 1-B: Waking Nightmare ( R1 : 8VP )
Dr Maheswaran joined the investigation
Dr Maheswaran is alive
Randolph escaped the hospital with the investigators

Upgrades:
2x Chicago Typewriter (4) for 2x .45 Thompson
1x Momentum (1) for Lone Wolf

The increased firepower was sorely needed since "Skids" O'Toole is the primary muscle, hence quickly upgraded into the Chicago Typewriter (4).
Would have preferred to use the Sawed-Off Shotgun (5) but his 3 makes it difficult to compensate for.

Scenario 2-B: A Thousand Shapes of Horror ( R1 : 6VP )
Randolph survived the descent
the investigators possess the Silver Key

Upgrades:
1x Momentum (1) for "Look what I found!"
2x Sure Gamble (3) for Narrow Escape and "Let God sort them out..."

The security provided by Sure Gamble (3) was vital.
I initially went with Eucatastrophe (3), but after failing miserably I found Sure Gamble (3) to be more consistent here given the +2 provided by the Chicago Typewriter (4).
Would prefer to have both though.

Scenario 3-B: Point of No Return ( R1 : 9VP )
Steps on the Bridge: 1

Upgrades:
2x Sharpshooter (3) for 2x Overpower
1x The Moon • XVIII (1) for Lucky Cigarette Case
1x Swift Reload (2) for Lucky Cigarette Case

Ideally I would have kept the Overpower, as it would have provided a little insurance early game before Sharpshooter (3) is played.

Scenario 4-B: Weaver of the Cosmos ( R1 + R5 : 5VP + 5 bonus XP )
the bridge was destroyed
the investigators are still in the Dreamlands