SET UP: Due to the unusual amount of missing person cases in Derry, Sam and Dean decide to track down whatever is exactly is the cause both believing it to be a powerful and deadly monster.
The two brothers quickly set up shop and take action.
Starting equipment: Impala, of course, Ruby's Knife, their various shotguns, and pistols and so on.
R1: No Losers Club with the exception of Mike Hanlon are around. Sam and Dean may use the information he has gathered about IT to aid their cause. Both have 1-week prep to learn all they can and enter the sewers to kill Pennywise.
Winchesters have Colt
R2: No Losers Club members exist nor can they be contacted for information. Sam and Dean must do all the legwork by themselves in learning about Pennywise/IT. Bobby and Castiel (original power levels) may assist them as well.