I guess you might put a great deal under contract first and then shop it around.The special knowledge that you would need would be the knowledge that the investors and agents would need. 

Are there a preponderance of check cashing businesses, pawn shops, businesses that do not support checking accounts but rather focus on a cash driven/non saving type of local economy? 

However, I do need to have a way out if once I shop it to my private investors they don't think it's a good buy.

The plumber says he wont check it out till all the water is gone , he has no boots , I ask if he has a pump , he says no he will have to go back to the shop .

From there you can window shop who your likely lender will be.

There is a pretty cool coffee shop in downtown Woodstock called Copper Coin which could be a good meet-up spot?

I have been shopping around for insurance on the property, but the quotes I am getting from insurance companies have annual premiums between $2700-$4500.

This is really basic but I'm going to be doing the majority or my "shopping" from California and only will have a realtor if it is suggested when my sister actually goes out there.

If you have a relationship with a broker/carrier - be sure they are shopping the properties accordingly.  

The area is so eclectic, there are what appears to be some professional ladies working the area as well as high end interior design shops on the same street.