I was kind of thinking mixing the cash out refis and private money covering my "skin in the game" with the funds from the cash out refi. 

Note that this doesn't mean they won't require you to have some skin in the game, and I question whether you could get funding for the deal you presented with the info provided.Hard money lenders are as different as fingerprints and, within the bounds of the law, are generally free to set their terms.

I did have to give him a lien against a separate lot that I own outright that is worth about $50,000 just so I had some skin in the game but I was able to do this without using any cash.  

They'll take you seriously because you have skin in the game.Jon,Most mortgage companies sell the loans to FNMA/FLMC.

Do you buy ugly houses? I have succeeded in negotiating a price for my first commercial property that made me quite comfortable. It is a mixed use building in a high traffic area. Currently it is vacant but one ten...

Then I negotiate where the investor covers purchase and holding and I cover rehab so I still have skin in the game, they like that.

I have some skin I can put in the game, but not much.

Me house hacking and living in the neighborhood that I invest in, puts more skin in the game to actually improve the neighborhood and lead by example

All closing expenses will be paid outside of funding.After I walk through these details I get the response something like “oh, you want 100% financing, aren’t you going to have some skin in the game?”.  

If you are going to find a mentor, find one who is willing to put skin in the game with you and offer the value that a true mentor should bring.