Conversation so far:
What were Daniel Boone's businesses?
A celebrity, Daniel Boone kept a tavern in Limestone, and also worked as a surveyor, horse trader and land speculator.
Was Daniel Boone successful with his businesses?
Daniel Boone was initially prosperous, owning seven slaves by 1787 (a relatively large number for Kentucky at the time), but began to have financial troubles while living in Limestone.
What happened to change Daniel Boone prosperity?
According to the later folk image, Daniel Boone the trailblazer was too unsophisticated for the civilization which followed him and which eventually defrauded him of his land.
What did Daniel Boone do after this happened?
Frustrated with the legal hassles that went with land speculation, in 1788, Daniel Boone moved upriver to Point Pleasant, Virginia (now West Virginia).
What did Daniel Boone do in Virginia?
In 1788, Daniel Boone moved upriver to Point Pleasant, Virginia (now West Virginia). There he operated a trading post and occasionally worked as a surveyor's assistant.
Did Daniel Boone take a more permanent position anywhere in Virginia?
When Virginia created Kanawha County in 1789, Daniel Boone became the lieutenant colonel of the county militia.
How long was Daniel Boone lieutenant colonel?

Question: Did he have any money issues?
Self-contained rewrite: Did Daniel Boone have any money issues after becoming lieutenant colonel of the Kanawha County Militia?