Q: "are you going to raise the rent?"

Homeowners without representation are likely to be foreclosed on much quicker compared to someone that does for obvious reasons: they don't how to defend themselves in a foreclosure proceeding, they don't know how to raise arguments in their favor, or how to negotiate.

And even then, those really experienced folks are able to raise capital by hiring intermediaries (aka brokers) who are specialists at putting together the capital stack (equity/cash from the LP/investor + debt/lender + co-invest from the GP/developer). 

It raised a couple of questions in my mind about the risks of wholesaling, namely the implications in the event that you assign a contract and the buyer backs out.It seems to me that Paid at Assignment would both:Result in committed assignees, otherwise they would risk losing the money they paid the assignor, andProvide the assignor with a significant cash cushion against breach of contract if they cannot locate another buyer prior to closing, and ultimately decide to cancel the contract with the property owner.But this raises another question. 

$370k capital raise with a bridge loan How did you add value to the deal?

We are able to raise our offer amount with a seller carry structure and that is what we use to convince them.

I ended up giving him some seller concessions (Which I ended up raising the price to make up the difference), he bought with a conventional loan, and overall was a smooth transaction.

A good deal could be that the upcoming vacancy presents the owner a unique opportunity to reposition and add value the property (basically finding a tenant that pays higher rent and therefore raise the NOI). 

We didn't do it and kept all tenants after the rent raise.

Pools generally don't raise property values but in general they do significantly increase STR revenue.