All Ears

I'm trying to self syndicate my column to as many newspapers as possible. I spent last few days compiling an email list of all the papers in Alabama, Tennessee, and Mississippi. The goal is to get the addresses for Georgia, Louisiana, North and South Carolina, Kentucky and Arkansas. I expect that will be upwards of a thousand newspapers. It's hard to know the best way to approach the decision makers at these papers. What makes them tick? Another concern is that I have no way of knowing how my columns will be received outside of Walker County. I've had a lot of people tell me the odds are against me but I've got to give it a shot.
I have recommendations from a number of people in the business and I'm working on a cover letter that is both catchy and compelling. I think if I can get them to read a few columns, I'll have a chance of getting published elsewhere.
If anyone out there has any words of advice, I'm all ears. I'm headed into uncharted territory and I can use all the help I can get.