UPDATE:
I recently got in touch with a friend of mine from high school. We had been texting back and forth, on and off, for the last couple months. It was the 2nd week of September, the week after the initial search for Kevin, and my friend mentioned how his car was stolen; he was given counterfeit money and the guy who he was selling it to drove off before my friend noticed. The car was a matte black 1999 Mitsubishi Eclipse.
My mom recently mentioned how Kevin had very little money in his bank accounts, indicating he probably withdrew most of it. One of the "rules" of disappearing is to only pay for things in cash.
Also, remember how I mentioned the SAR dogs were able to track Kevin's scent all the way down Mt. Herman Road, only to lose it suddenly near the Monument Hotshot Center? As if Kevin got in a car. Maybe he had a ride prearranged.
My friend said the man who he was selling his car to was dropped off by someone in a white pick-up truck. My mom mentioned how Kevin knew someone from working for the town of Monument who would give him rides to and from work. This coworker supposedly drove a white pickup. I know, there are many people who own white trucks, but his just adds to the coincidence here.
I decided to pursue this further and asked my friend several questions. My friend said the transaction occurred around 8pm, Sunday, September 2, in the Monument Safeway parking lot. The man appeared to be in his 20s or 30s, though he admitted he was rather bad at judging age. The man had long-ish, brown hair, a bit of scruff, average height, about average weight, and didn't talk much. He asked the man his name, and the man hesitated, then replied something "very generic." My friend thought nothing of it, though. This description somewhat matched that of Kevin. Although he does have red hair, it is a dark-red, that could easily appear brown in the dark, or when its just long and greasy. I showed my friend Kevin's picture, and he said "Yea the guy kinda looked like that." The man was wearing a dark hoodie, pants, and generic black shoes. Kevin could have easily had these clothes with him to change in to. My friend also said that the man was terrible at driving stick-shift. As far as we know, Kevin didn't know how to drive a stick, unless he had learned back in Wyoming. He may have also had a Wyoming ID.
My friend had also removed the plates prior to selling the car.
As far as I know, this friend knew who Kevin was, but did not know him very well. I do not think he would be able to recognize Kevin in his appearance at the time: long hair, some facial hair, taller, and heavier than Kevin was back in high school, when this friend would have been most likely to see him the most.
So here is a theory, and I must emphasize that this is just a THEORY:
-Kevin left for a hike Sunday, September 2, at 8:00 am
-Kevin was picked up on Mt. Herman Road by his coworker. Maybe he had another cellphone to arrange this, or maybe he just hitchhiked with some stranger. Regardless, he was driven to Safeway to buy this car which he found on Craigslist.
-Kevin buys the car from my friend around 8:00 pm, gives him fake money, and then speeds off.
-My friend calls the police, but Kevin is long gone, probably out of the county.
I think this was a very strange coincidence; that all of this happened the day Kevin went missing.