A stint in prison can explain why your ancestor is not enumerated with his family in the census. Court records or newspapers may contain additional details about why your ancestor landed in prison. State prisons (or the state archives) may have additional records. And, it is also possible your relative ended up divorced over his incarceration–resulting in more records.
Genealogists often require help (in large and small amounts) from other genealogists. Sometimes it is a quick lookup in a record and sometimes it is a more extensive “look” at a problem in order to get some advice.
Remember that the sharing goes both ways. Offer to help someone with a research problem, to take a picture of a tombstone, or to make a copy from a book that you have.
Getting away from your own research problems and looking at someone else’s often gives you insight into your own.