If the lender is requiring you to put 30% down on a flip, its likely because the deal itself doesn't look great and they would want you to put more 'skin in the game'. 

@Daniel Stoychev for me personally I’m open to investing most anywhere if the deal is right by the choice between Cook County or not Cook county I will always go with not Cook County. 

I personally don't like condos for a rental property.HOA feesHOA rules that can change.

So instead of paying the bank for a home equity line of credit on my first home and paying them interest, I was able to use a personal loan to myself via my employer 403b and pay myself back with interest. 

Correct, which means that "not on your personal record" is not actually factual.

My game plan is to do a house hack as I have very little capital.

I personally don't have enough funds to come out of pocket.

He said, "I know it doesn't cash flow - but I just want in the game!"  

Wouldn't the same capital gains tax liability exist if I kept the property in the s-corp and sold it in 10 years vs. moving it out of the s-corp (into my personal name or an LLC) and selling it in 10 years?

I also know that in many cases the llc will protect my personal assets and I fully believe this is either analysis paralysis or just fear of failure.