It has been a while since I've worked on my Bailey Line.
I looked back into my records and found 5 Bailey's named Isham.
The Isham whose wife or wives I am trying to identify was born about 1753/1755 in or near Albemarle County, Virginia and died in 1835 in an area of Kanawha County which would later become Putnam County.
This Isham has a RW pension record which greatly helps to establish the approximate year of his birth. I believe the Isham you are looking for was the son of the 1753 Isham.
He was born about 1791 and lived to the mid 1850's. I believe you will find him enumerated in the 1850 Putnam County, Virginia Census. I also think there is a War of 1812 record for Isham Jr..
My records indicate that the Isham born abt 1753 had the following children:
William Pleasant b abt 1775
Mary Mildred "Millie" b abt 1779
Elizabeth "Betsy" b abt 1781
Winona "Winnie" b abt 1785
Sarah b abt 1789
Isham Jr b abt 1791 married 1812 Kanawha Co., Nancy Joplin
Hezekiah b abt 1793
James M. b abt 1795
Martha b abt 1801
Isham's wife was either 4 or so years younger than he or later children may have had a different mother??
Isham born abt 1806 seems to be the son of Henry Bailey
Isham born abt 1812 who married Lucinda Smith seems to be the son of William Pleasant who was the son of 1753 Isham.
Hope this helps rather than confuse.