For a quarter million dollars though, don't you tolerate having swollen feet for another week or two?
I've thought a little bit about how I would play if I were ever on the show. (And since it doesn't seem like a show that will have multiple seasons, I don't think posting this has any risk of giving away my strategy if I actually did appear. But if that's wrong may need to desperately delete this post in a year or two.)
First, all the people who are closest to me and very obvious would be my Diversion Team. The people I hang out with the most, my immediate family. They'd have no real idea where I was, but they'd be using burner phones, calling each other. Sending emails to each other with random babble that looks like secret codes. If they had the time and it wasn't too inconvenient, driving into the middle of nowhere and back for no reason.
My real team would be people I have reason to think would be loyal but am not in frequent contact with. Extended family, former coworkers, friends of my mother from her coop housing development. People who I don't talk to frequently but I either used to talk to frequently or talk to a family member frequently. When I signed up for the show, before the hunt started I'd find ways to talk to them face to face and ask for help. Like, go to game night at the housing development and talk to her friends who know me without her knowledge, find out who might have a summer home or something I could stay for a few days. Nobody who was actually helping me would know who else was helping me, they'd get a call, pick me up, drop me off, I'd walk a mile or two and somebody else would pick me up. Maybe they'd drop me off near a Greyhound bus station just to make them think I took the bus.
Assuming that if I was on the show it'd be near my home, the New England area, I'd keep the Appalachian Trail as a fallback. If I thought all my plans were compromised, I'd have somebody drop me at a trailhead near the part of the Appalachian Trail in Maine, the stretch in the middle of nowhere where in some cases people haven't been found who have desperately wanted to be found. (I wouldn't be afraid of getting lost cause camera guys would be there). That way, even if they figured out where I was odds are they couldn't find me. I wouldn't try to do that for 28 days, but maybe the 10 days after all my other connections were figured out.