with someone that according to their own friend doesn't have high self or dating esteem.
where in ANY of what he's typed leads you to believe that he might be a suitable partner for your wants/needs?

then you make it about you (in the wrong way) with the statement about being perpetually single and that you would date yourself.
That's great
however we're talking about someone else with their own issues and quirks that have nothing to do with you. Those issues that impair their dating experiences were there before you got there and more than likely will last longer than your situationship (i hate that this is even a term nowadays but when the shoe fits...).

don't be so focused on the end result (serious relationship) that you lose sight of what's needed to get there.