He says his wife handles that side of things.It makes it awkward to call him for a new job knowing I still owe him from previous jobs.

I would add that working with a hard money lender may be advantageous to working with private money when you are not an expert in REI, because an HML will only fund a deal they know has a good chance of succeeding, whereas some private money may accept a deal you tell them is good, but then if you miscalculated things can get very awkward very fast, especially if you have a strong personal relationship with your private money provider (e.g. if they are a close friend, or a family member). 

In many cases, my properties do have current occupants, so it becomes a very awkward situation for the occupants if they are surprised by a stranger in their yard.

I find myself often getting stuck in long, awkward, drawn out conversations with these people because I'm trying to figure out what to say even though I can tell they aren't interested. 

If I wait what would I do with that awkward time where I have no place to live while I look for a deal?

Hiding behind an entity like an LLC can place him in awkward position if disguised from other heir/bene.

Awkward.

If they through in a couple of months of Sat radio, toolbox, and oil changes for a year, then it makes sense I personally find (in any service industry) additional fees without a service rendered, awkward and unjustified.There must be another agent without the fee that does exactly the same thing.

Any suggestions as to how I can have them move, without it being awkward? 

It seems like I'm the awkward guy at the high school dance not a jock and not a geek so I'm kinda in the middle with no true social group.