Kirby;
I suspect you have seen this but for others and FWIW
https://thelibrary.org/lochist/history/reminis/mogov.html

He had enough pull to use the Military Telegraph to message President Lincoln.
https://www.loc.gov/resource/mal.1306100/?st=gallery

Orr was elected Major of the Phelps' Home Guard at Goose Pond. This being Congressman John Smith Phelps, who organized a Pro Union Regiment early in Greene County. Marcus Boyd who figures prominently with Orr was elected Lt Col and Pony Boyd as the other major. See The Battle of Carthage:First Trans-Mississippi Conflict of the Civil War byKenneth E Burchett pages 12 and 13.
Orr at that stage was pro-Union, anti-emancipation as were many who saw the conflict early on as less about slavery and more about secession. He telegraphed Lincoln about 6 months after the the Goose Pond meeting.

Orr was accused of robbing a bank in Springfield of $24,000 to keep the money out the hands of Confederates; see: https://mdh.contentdm.oclc.org/digital/collection/mack/id/5477/
This being shortly after Wilson's Creek.

From Missouri Politics During the Civil War;Laughlin pg 29-31
"The Constitutional Unionists first nominated Robert Wilson for governor but he declined because of old age and poor health. Sample Orr of Green County announced himself and was well received by the Constitutional Union press. Orr was a little man, freckled-faced and red-haired but almost single-handed he put up one of the most memorable campaigns in the history of the state.
For keen logic and biting, sarcastic wit he has seldom been surpassed on the American stump. He took the position that the slavery question should not be agitated but came out strongly for state aid to complete the trunk lines in the state. He was also opposed to their sale. He attacked Jackson on the issue raised by the "Jackson" Resolutions and took a decided stand for the preservation of the Union.
17
La Grange National American, July 21, 1860"

Orr's tune was more strident by Oct 1862 when he gave a speech supposedly advocating for succession generating a letter by HM Sumner to Gen. Benj Loan at Lexington asking for approval of Sumner's action to restrict Orr to Jefferson City MO see: https://collections.shsmo.org/manuscripts/columbia/c0510

Sumner was acting Provost General at the time.

This leads to Orr's testimony in Thomas Price vs McClurg recorded here
https://books.google.com/books?id=025HAQAAIAAJ&lpg=PA168&ots=zoxj8M3m33&dq=hm%20sumner%20jefferson%20city%20mo&pg=PA165#v=onepage&q=hm%20sumner%20jefferson%20city%20mo&f=false

This testimony of Orr describes pretty well his actions and viewpoints that drove them during the war. It is fascinating to read.

In 1920 History of Missouri Orr's reputation was reported as such:
https://books.google.com/books?id=7X8UAAAAYAAJ&lpg=PA97&ots=E7oUrc4B4i&dq=sample%20orr%20missouri%20politician&pg=PA97#v=onepage&q=sample%20orr%20missouri%20politician&f=false

William Hyde, editor of “The Republican," writes of Orr as follows: “Claib Jackson finally emerged from the hickory-nut country, but was loath to come out of his own shell. A man named Sample Orr, of whom nobody ever heard before, had, immediately after the Baltimore Split, saddled a horse somewhere down in the Southwest, put some light clothes into a pair of saddle-bags, announced himself as a Constitutional-Union candidate for governor, and started out on the flank of the Democratic candidate. Of course every body laughed at his temerity and when they saw him they laughed all the more. Nobody knew of any backers he had, of any antecedents, any records. He was nobody's nominee; just plain Sample Orr, farmer. Very plain he was. He was a freckled, strawberry blond, and there never was any thing redder than his hair. A man of medium height, slight build, weight about 145; keen blue eyes, white eye-lashes, nervous, short step, stooping shoulders, long neck-another Ichabod Crane. Where he concealed his voice was a wonder, for he could be heard a good distance and his speech was charming."

So at best Sample Orr appears to be a rather small merchant farmer who was active in Greene Co politics in the 50's being a Probate Judge. He was well enough connected politically ending up in Jefferson City after the removal of the Jackson government, likely due to his animus against Jackson. He remained anti-emancipation, pro-union, a position becoming untenable by 1864.

Not what you asked for but the closest I can come. I can work up his family tree if you wish.
JJR