Getting incarcerated first was definitely my first thought as I read the conditions. He wants to control the environment, so putting yourself in a low-security jail insures that you will be watched and decreases the likely hood that the living conditions of the inmates are so bad that they can be paid off. The more I thought about it though, the more I could relate it to another problem. "If I knew I was going to be stabbed, would I stab myself first so that I'd put myself in the hospital near doctors and/or if I was the pre-determined stabber, then I consciously controlled the entry point thus avoiding my death?" I don't like the argument, so I scrapped it.
You might go a whole Chris-Pirillo approach on the whole deal and livestream 24/7 but that's a little impractical. Let's assume I have a job outside of my house that I need to attend.
The only way I can think of is to have a set amount of check points you have to go through that change periodically. So let's say that you have a 30 minute drive to work. Well, it'd be safe to assume that you can stop twice on the way at places that do have cameras and/or at the very least, a place to buy things that give out receipts. The intervals of time, along with periodically changing your route (to remain unpredictable) should be proof enough to hold up in court that it'd be physically impossible to do whatever it is that this "bad guy" said you did.
However, the whole premise of the idea has a flaw. If he has the financial backing to totally screw you over...I'd imagine technology is the last place you'd want to go since the more money you dish out, the less secure technology becomes (as in...you might be in Wisconsin but he has the money to make it look like you were caught on camera in New York).
