Well, since I'm studying Decision Analysis this semester, I'd quickly intuit a couple of key factors:
1) Is either of them out of range of my rope? If one is, he's phucked.
2) Is either of them heavy enough that they can threaten my leverage position and drag me in with them? If so, he's phucked.
After that, DS has a family, and lives in Durango.
CM doesn't have a family, and lives in Wyoming.
From a humanitarian standpoint, I go for the guy with the kids.
From the "crash-pad" standpoint, I'd much rather crash in Durango for boating opportunities than Wyoming.
CM is phucked, assuming there's no clear answer in questions 1 and 2.
"self-aggrandizing jackass" - it says it right on the label