The 1840 Henderson Co Ky census has several listings for James Connaway:
HH #229 James Conaway (20-30), 1 (15-20)m, 1 (10-15)m, 1 (70-80)m. Four people total in household, three in agriculture. There are no females listed. I believe that the oldest male is John Connaway b~1770, the first Connaway in Henderson Ky. According to this entry, James was born ~1810-1820
HH #232 J---- M Connaway (hard to read) (20-30) m, 1 15-20f , 1 under 5f. I believe this is James M Connaway and Lucy Ezell who married in Henderson in 1839. According to this census, he was born ~1810-1820 and his wife was born ~1820-1825. The child was born ~1835-1840.
Also on the 1840 Henderson census is William J Connaway hh #219 age 20-30. He is living with his wife Jane Ezell and their children. This is my direct line.
James Connaway and Lucy Ezell are on the 1850 Breckinridge census as follows: James M Connaway, age 32, farmer born in Virginia; Lucy E, wife, age 27; Sarah R age 7; Francis M age 5; John R age 3; Mary J age 1.
Henderson tax lists 1836-1841 list James Connaway with a water source of Canoe Creek. In 1837 he sold 183 acres (Deed book I page 56) The 1840 tax roll taken in June has John Connaway on Canoe Creek (John sold his land on Lick Creek in Jan 1840). This matches with the 1840 census HH# 229 .. John sold his land and moved in with James... his son?
I do not know who all these James Connaway's are. I know they are related, but haven't sorted it all out. How is James Connaway on Canoe Creek related to James Connaway who married Lucy Ezell? Are either of them the son of James Connaway who married Rebecca Royster in meck VA in 1816? I think so.
I think James and John Connaway are brother (the older ones). I think both families came to Henderson at some point... some briefly and others stayed for generations.