Boone was initially prosperous in Limestone, owning seven slaves, a relatively large number for Kentucky at the time. In 1786, he purchased a Pennsylvania enslaved woman, age of about 20, for “Ninety poundes Current Lawfull (sic) money.”. A leader, he served as militia colonel, sheriff, and county coroner. In 1787, he was again elected to the Virginia state assembly, this time from Bourbon County. He began to have financial troubles after engaging in land speculation, buying and selling claims to tens of thousands of acres. These ventures ultimately failed because of the chaotic nature of land speculation in frontier Kentucky and Boone’s poor business instincts. Frustrated with the legal hassles that went with land speculation, in 1789 Boone moved upriver to Point Pleasant, Virginia (now West Virginia). There he operated a trading post and occasionally worked as a surveyor's assistant. That same year, when Virginia created Kanawha County, Boone became the lieutenant colonel of the county militia. In 1791, he was elected to the Virginia legislature for the third time. He contracted to provide supplies for the Kanawha militia, but his debts prevented him from buying goods on credit, so he closed his store and returned to hunting and trapping, though he was often hampered by rheumatism.