Keep in mind that the charter industry is very fragmented. There are mom and pops operations operating all over the country with one or two airplanes. You can't compete with the guy who has 25 airplanes scattered throughout the country, ready to repo a short leg on a minute's notice. If you start a charter operation, you need a large amount of local business. Otherwise your rate to repo from Augusta, GA to TEB, then fly some dude to MDW, then repo back to home... your rate will not be competitive. And if you break along the way, you've got no backup. Unless you have identified a market niche in your local economy, you are setting yourself up for a miserbable experience to cost you much much money.

Yes, I am the guy who knows everything and quite literally invented the charter industry with two Wright Flyers back in 1910.