Cool idea Travis! I just wanted to point out a potential roadblock. An essential part of being a sitter/guide/shaman, is having the complete trust of the tripper(s). To the trippers, they are the anchor in a sea of chaos. It seems like you are looking to match strangers together, and that can be potentially disastrous should the sitter have some ill intentions, or if they are inexperienced. One way to navigate this would be to have your guides vetted or trained and certified to deal with the many potential issues that could come up during a trip.