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Like your other respondent, Wirt Woodson would be an ancestral second cousin to me, and also like her, I do family history, not genealogy.
There doesn't seem to be much if any help on the Genweb site for this county.
If you haven't tried it yet, I would contact the public libraries in Poseyville and Evansville (Willard Library) to see if Posey County cemeteries have been indexed. I do not recall whether Posey County marriages have been published, but you might ask them about this as well. The more information you are looking for, the more likely you will be required to hire someone to do your lookups.
A lot of what you are looking for would be relatively easy to find using the census records, and the 1880 census can be searched free at familysearch.com.
Another strategy which has worked for me several times is to try to locate a descendant in the area. Specifically, look on a site like whowhere.com for any Woodsons living in Posey Co., or send a letter within a letter addressed to the postmaster in New Harmony, IN. The letter to the postmaster requests that the letter within be delivered to anyone of the surname Woodson or a descendant of Wirt Woodson if the postmaster knows of one. The interior letter is a request for information on his/her family to the Woodson descendant. It should be in a separate envelope with postage on it. This has worked for me several times. Of course, there's always a chance that the letter will be returned if the postmaster can't locate anyone. I suppose I was lucky- that never happened to me and I have been able to locate descendants of siblings to as far back as g-g-g-grandparents this way.
As a courtesy, and to facilitate a response, it would be well to include an SASE with the request for information from the descendant.
I have been to the courthouse in this county once a few years ago. It is, or was, one of those courthouses where they send you to a little room almost like a jail cell in the basement.
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