A bit loaded sentences, I guess. Still, do they sound correct to you?
1 I asked Marvin yesterday about a man he might have known to have lived the longest in this settlement.
2 I asked Marvin yesterday about a man to have lived the longest in this settlement of which he might be aware of.
3 I asked Marvin yesterday about a man having lived the longest in this settlement known of by Marvin.
1 I asked Marvin yesterday about a man he might have known to have lived the longest in this settlement.
2 I asked Marvin yesterday about a man to have lived the longest in this settlement of which he might be aware of.
3 I asked Marvin yesterday about a man having lived the longest in this settlement known of by Marvin.