The interesting thing I realized about the characters in "Halos & Brimstone" and "Supernatural" is this:
Barry and Mak are the love children of Dean and Cass
Imagine if Dean and Cass made sweet love and had some babies. What would they be like? Mak and Barry is what they'd be like.
Mak is a goofball, just like Dean Winchester, but he's got the power like an angel ( or, in his case, a demon). He loves women. He loves food and beer. He loves cracking terrible jokes. Mak is Dean with Cass' power.
Barry is a goody-goody, always following orders, just like early Cass. After awhile, Barry starts questioning God and the rules, and he takes matters into his own hands...just like Cass. They spend some time contemplating what to do. The big difference is that Barry doesn't swallow up a crap ton of souls and nearly smite the entire world. Barry has Cass' emo side, but keeps a clearer head like Dean.
What a happy family! :)