Personally - I like the idea.
This is a project that wouldn’t require a large production team. As an example - Julie Powell (sp?) became successful just by cooking her way through Julia Child’s cookbook and writing an entertaining blog about her experience. The example here is that with YouTube and other blogging sites you are capable of reaching millions of people all by yourself! The trick, of course, is to be very entertaining while also providing some commentary on our society of consumerism. You would need somebody to assist you that can take your raw footage and turn it into a story that other people would actually want to watch.
I would suggest that you don’t just start this thing cold turkey. Have - at least - an outline of what you will do, when, and have a set of backup plans ready to go. You would also need to have an agreement with some of the earlier businesses you’d be working in since they will probably frown on you working there while carrying a video camera. It would be better to get that sort of negotiating out of the way before Jan 1. You may think this is cheating but watching you living in a trash dumpster eating leftover Wendy’s for 6 months will not be entertaining now matter how you edit the footage. Plus, since you have actually stated a target of one million dollars, you need to come across as a person who can actually attain that goal. Nobody will stick with you if you only have $150.00 to your name after 6 months. And as long as I’m commenting on things that will kill your video, I’ll throw in your idea of starting naked which I think is just pandering. I can’t imagine people taking you seriously as a financial and social commentator what that is their first impression of you (unless you are Allison Hanygan at which point that will be fine).
If you play the show correctly it could be very educational. Most of us have access to far more money than we realize - we just spend it so quickly on mortgages, car payments, consumer goods, and other “necessities” so that we never notice just how much we have. If you spend a year living far below your means you’ll be able to show that there is a way to treat money where it actually works for you as opposed to credit or debt which will just enslave you to it. Your show might prove the old adage “it takes money to make money”.
With a good layout and plan - I think you could have something.