Actually, you should be able to get concrete, data-based information on every aspect of a TK operation - lack of prompt and transparent communication is another massive red flag.I think the greatest argument against self-assembling a team would be that each entity has limited skin in the game.

Personally for flips in LA County 100,000 comes in handy to just even put some skin in the game on an investment property with a hard money or private lender.

It also means that most of these entities have limited skin in the game - meaning they just need to move through the part of the investment that gets them paid.

I am looking for TK providers who own their PM firm as I believe they will have more skin in the game as they are servicing a property they sold.

Even hard money/bridge financing will want some skin in the game. 

I guess your "skin in the game" is you purchased the house...

I believe I do trust him, just trying to figure out how to get the work done and him  have some "skin in the game" as well.

You can do it, but you need to be a problem solver have some thick skin, in many cases.Also, in some cases your hands may be tied from a regulatory perspective. 

What would be enough skin in the game to make all parties comfortable in working with a newer player?

They do this on purpose so that:Lenders in general do not like loaning money to people with no skin in the game.