As an American, basically you have more or less the same two routes as someone looking to enter the US from abroad: job or family. For a long-stay visa of the non-working variety, you have to have significant financial resources - enough to convince TPTB that you won't even be tempted to work, or be of retirement age with a decent pension.

Finding a job in France is tough no matter what your circumstances. You need to have a decent command of the language at a conversational level at the very least. Education and insurance sales are not in high demand here, as education is more or less a "civil service" function and the insurance business is quite a bit different than what you find in the US.

One option is to come over as a student, both to improve your French and to be able to scout out the job situation on site. Chances are you will have to go back to the US for some period of time, even if you find a job, but having studied in France will give you something of an "in" on the visa track.

Find the website for the French consulate that covers where you live (probably in Chicago) and study the information they have on visas on their website. It may give you some ideas.
Cheers,
Bev