If any contractor who specializes in foundations were interested they'd probably strike gold there.Aside from that, the numbers.

If I see in the tax records that someone owns multiple properties, I will attempt to reach out to them (preferably call) and strike up a dialogue.  

Now friend 2 I would try and strike a deal with him.

What I am hoping is that we will strike an agreement that will be favorable to both parties.I don't think the Title company will insure the title without clearing this note.

If you decide to allow it with the pet agreement/deposit/rent increase, then be sure to have a frank conversation with him that the dog situation is not cool and you will be keeping an eye on his tenancy and this is a strike against him. 

On top of the LL approval there are often clauses stating that any profit earned in a sublease must be split 50/50 with the landlord and any attempt to strike the language is generally a red flag. 

Not going to strike it rich that way over night, but building a foundation and learning should lead to success.

I asked the timid tenant to make an effort to be more neighborly and perhaps try to strike up a conversation from time to time with his neighbor.

And ofcorse the Big One could strike any time.

But something here strikes me.