If you are stuck on a record, learn something about every person named on it, particularly those who you do not think are related. Witnesses and other people mentioned in the document may provide clues to your ancestor and his life. It is not always necessary to learn complete life histories about everyone name on a document, but some research on others named cannot hurt.
If your ancestor signed a deed, who were the witnesses, who was the notary or Justice of the Peace in front of whom your ancestor acknowledged the record?
Finding out a little about the others named in the record may help you learn more about the record and your ancestor.