Karin, Most of the people you name I can find a relationship for. I haven't researched these particular families further - the info comes from "The Trueblood Family in America, 1682-1963" by Bula (Trueblood) Watson.
Malachi (your #3) and Edmond (your #4) are half first cousins. Malachi is the son of James and Agnes (Proby) Trueblood. Edmond is the son of Joseph and Letitia (Willetts) Trueblood. James and Joseph were half brothers, both the sons of Josiah Trueblood, but by different mothers. Josiah is the grandson of John and Agnes (Fisher) Trueblood, of which many messages exist on this forum.
Back to Malachi (your #3) - the book has him b. circa 1806, m. 1828 in Pasquotank Co., NC to Sarah Trueblood (his 2nd cousin) and dying before 1850. Indeed, Sarah remarried to Solomon Pool. Malachi emigrated to Wayne County, IN, then to Madison Co., IN. I do not have an Ann E. or Madison as children of Malachi and Sarah, but have Thomas (your #8 & #9), Stephen, Hezekiah L. (your #11), and Eliza (who might be your Ann E.). I have some further info on this family.
And back to Edmond (your #4) - the book has him b. circa 1782 in Pasquotank Co., NC and having 5 children, among which are Amos (your #6) and Edwin (your #7). Again I have some further info on this family. Finally, Wilson Trueblood (your #5) is an older brother to Malachi (your #3). He married Millicent Trueblood (a sister of Sarah Trueblood, who married Malachi) and had 3 known children, including Wilson Thompson Trueblood (your #10). More info here also.
Your #1 and 2, I am not sure about. The Pritchard family intermarried with the Truebloods quite often, but I'm not familiar with this one. And your #1 rings no bells. All a little confusing, but I hope this helps. Contact directly if you need further info. Charley Talbert Lancaster, PA