After reading and reading, listening to the podcast twice, researching all characters involved and as a gay man myself having come from a similar background, I am of the opinion Jake was in great conflict with himself as a closeted gay man. It is not just one clue, it is all the clues together which make me believe this. The close friendship with Ken, spending time with him while married, why did Jake's marriage fail? what was the mysterious reason for her to resent Ken? He lived in a small town where homophobia would reign, Jake tended to be embarrassed about things, Gary (the last person who saw him) is gayer than a 3 dollar bill, he is currently out in Seattle working as a hairdresser, this also explains why Gary has not be forthcoming, he is keeping Jake's secret as promised, Jake just wanted to run, be free, be who he was, maybe even turn trans, i think he was in love with his friend ken and was totured over that, ken who is very straight would have been clueless and also disgusted if he ever found out, i would imagine that he fooled around with Gary, Jake's ex wife is also rather quiet and accepting of it all, they got along so well yet couldn't stay married? Jake already has a very feminine look, he had very feminine attributes. Described as "playful" and silly/crazy. You don't describe straight men as "playful." In the pictures he's 31 - he looks 12. Not a hair anywhere, did he shave? he was sensitive, didn't like the boys he was babysitting to fight, fed up with being a mechanic, probably a profession that hid his secret really well, Jake like to go to parks alone (that is totally a stereotype, but hey), Jake didn't really date, the supposed new girlfriend he had has never been seen, he hated being a mechanic but the military is also where gay men who feel they must keep their secret go to "come off straight." I would like to know what drugs he was into - it could give a clue, guys like Jake would have been drawn to ecstacy, meth, coke, his catholic schooling would have made it clear that living as a open homosexual would mean eternal hell, at ken's beck and call for cigarettes and snacks while at work (30 year old straight guys don't dote on another guy like that especially ones that have two kids a job and school AND in the National Guard AND a supposed girlfriend). Again, just my opinion and it makes all the sense in the world. Happens more than people are willing to believe - we are not even close to truly accepting gay people as equals, especially in small towns. People live in terror of being found out and in silent torture not to be free to be who they are, love who they want to love, you know just be normal like everyone else around them. Therefore, some people are not ever able to come out to their family and friends, Jake was too embarrassed even to tell anyone he wrecked his car in exactly the same place, think that kind of person is going to feel comfortable coming out in Po Dunk, Michigan? His age is a clue as well. 31 - he's had enough of hiding and finally just can't take it anymore. Doesn't want to answer any questions or have any one follow him, he's out, free to live a new life as the person who God made him to be. I do hope he's alive... the Social Security issue does bother me, but he could have gone totally off the gird - living on an Indian Reservation - laws are very different there. Maybe in New Mexico (he did head west), left his car on the side of the road, and hitched a ride, the last leg to NM so as not to not leave a trail to his final destination, Mesalaro Apache Reservation is due West from Sweetwater, the car got stolen and taken to Mexico where it was eventually trashed... I hope this helps in some way.... it truly makes sense if you consider the emotional and psychological pain he was probably secretly in. OH one more thing - the sighting in South Chicago... probably spotted at a gay bathhouse or gay bar. The guy who spotted him didn't want to be identified because he admitted he wasn't supposed to be where he was, but being scared about being caught by his wife visiting a sporting goods store makes absolutely NO sense. It was good of him to call anyway, even if it couldn't be verified. Ok, i think that's really it....