The most obvious new upgrade for Roland has to be Shortcut. Prepared For The Worst is good for weapon searching, although with six weapons, you'll have a decent shot of having one at the start anyway.

This might be controversial, but I feel like Inquiring Mind has good synergy with Roland. His character abilities encourage him to fight in places with clues, and Inquiring Mind also feeds on that. Plus three fight on a test is great!

Gotta keep Vicious Blow for sure, and I like Emergency Aid to heal up his soaks or let Guard Dog do more damage. Art Student might also be a good one for Roland as a cheap soak and clue.

Upgrade Path

New Vicious Blow seems busted. Upgraded Beat Cop also synergizes really well with Emergency Aid. Charisma and Brother Xavier could be great choices for Roland as well, lots of supportive ally possibilites.

Lightning Gun is the big boiii bruiser, and Extra Ammunition ensures you can use it a lot.

Pathfinder could be really nice if you feel like you need extra movement. Police Badge might be good to use with Lightning Gun to take one turn and demolish a boss.

Could throw in Elder Sign Amulet or Smoking Pipe to help him deal with his low Sanity value.

Stand Together and I've Had Worse help with resource generation, which is vital for this deck. Lots of high cost assets to pay for.

Not sure if Red Gloved Man would work that well for Roland, don't feel like there's as much synergy.