Do you have approximate dates of birth for the children of the brothers J. Geo. & H. Michael VALENTINE? If they married late, the following might connect. MYERS' Marriage Licenses of Fredk. Co., MD, VALENTINE:

Jacob, 2 Je. 1779, Mary FREE [Could Jacob be J. Otto, m. FREEZE?]
Henry, 21 S 1779, Eliz. FREY [FREEZE?]
George, 22 May 1787, Mary STULL [Anna Mary?]
George, 1 Jan. 1807, Eliz. KNOUFF
Elizabeth, 30 Oct. 1809, Joseph OGLE
Jacob, 14 Oct. 1815, Rebecca PICKING
Fredk., 11 N 1817, Catherine BOWERSOX
Barbara, 30 Apr. 1818, Henry DEAVER
Mary, 12 S 1818, Jacob CROUSEE
Magdalena, 15 Apr. 1820, Jacob FIROR
Samuel, 19 N 1822, Eliz. MARTIN
Solomon, 22 S 1824, Magdelena BIRELY
Henry, 2 May 1825, Margaret SMITH
Fredk., 18 S 1826, Eliz. LEAB
Wm., 3 S 1827, Mary Magdelena MARING
David, 16 F 1829, Margt. CRUM
William, 8 D 1830, Lydia MEARING
John A., 23 Aug. 1837, Susan HARP
John, 26 D 1837, Lavina HARBAUGH
Sarah, 1 Mar. 1838, Peter WARENFELS
VALLENTINE, Sarah, 4 Jan. 1810, Jacob DELAPLANE

W. MD Newspaper Abstracts: 23 Nov. 1808, Independent Am. Volunteer, Fredeerick: John VALENTINE gives notice that he will pay no debts contracted by his wf. Esther, she having absconded from his house...