The miskatonic G-man who likes high shroud locations

Roland is an atypical investigator:

1. He likes high shroud locations, because he doesn't need to test his Intellect to get the clues (Working a Hunch, Scene of the Crime, True Understanding, Art Student, killing enemies for clues), and he can Crack the Case and earn lots of resources for himself or his team.
2. He also likes enemies in those locations to get the most of Scene of the Crime and his ability.
3. Finally, he likes to handle his friends' encounter cards, in order to understand better what is going on.

To prepare for high shroud locations is easy, just make sure you have the cards mentioned above in 1. to gather the clues, and the resources to pay for it.

But before that, you need to get ready for any enemy, you are, after all. The guardian of your team. If you got a .45 Automatic or Roland's .38 Special, place it as soon as possible. If you have no weapon, use Dr. Elli Horowitz to find Enchanted Blade if possible. Once you're ready, get to those high shroud locations and go On the Hunt.

Roland is not great when it comes to handling Willpower and Agility tests. As soon as possible, try to get a Tooth of Eztli - it's much better if you get it through Dr. Elli Horowitz, so reshuffle it if you got it in your starting hand; the reason for this is that you can have both the Hallowed Mirror and Tooth of Eztli in play then. Once you're set, you can easily beat most encounter cards of your team with "Let me handle this!" and get a clue via True Understanding. Take the Initiative is mostly there to help pass such a test if needed.