In 5) the meanings can be different. "having 3 houses" usually refers to the present situation, but in proper context it can refer to the past. "having had 3 houses" can only refer to the past.
a) I don't think "come with me" is strong enough to qualify as insisting. Also, insisting implies telling you more than once, even after you said you didn't want to go.
b) The correct sentence is, 'He insisted on my going with him.' The rule is that a noun or pronoun modifying a gerund must be in the possessive form. However, most native speakers say 'me'.
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