They will want to see why it isn't selling and they will also probably want more skin in the game.

Glad you have thick skin :)  DO NOT do this deal unless you can get it for 20k less. 

It is not common that a lender will issue a cashiers check but you also mentioned that you don't want to dip into your emergency fund, so you'll need your "skin in the game" somehow. 

Communication has always been the sticking point for me as I am not quick to trust my investment to someone with no skin in the game and who hasnt' gotten my ok on spending my money.In my mind it might be better to find a realtor or other money partner in long distance properties and pay them a management fee for that service. 

I have done 2 successful flips and also have one 1 buy and hold.Now that I have a little skin in the game I’d like to ask my dad who is 62, with a 6 figure 401k to allow me to use $50,000 to invest in more real estate.

I will say they are pricey ( that's why they call it hard money) and you would need to have skin in the game.

You're going to have skin in the game and lenders will look for it and check your DTI, credit history, employment history, bla bla if you buying in your name.

Having someone with some skin in the game has been a good option. 

Consequently, I am exploring the option of bringing in a local investor as a partner who will have a vested interest in managing the property effectively (skin in the game). 

New investor with skin in the game.