Required good credit, adequate reserves, full doc commercial loan with a personal guarantee.  

Difficulty in getting a second loan?

I can go Home Equity Loan route: HEL would equate to roughly a $600 monthly payment (dependent on rates).

If you are setting aside funds for capex, taxes, insurance, or other expenses that don't occur monthly, transfer those funds to Savings each month and hold them there until it's time to spend them.

Assuming property taxes + insurance added don't go above $1,100 total, you could maybe make this work. 

My question is around property insurance and specifically what are everyones MUST HAVE COVERAGES. 

I'm thinking I can use a VA loan to purchase a multifamily in FL and house hack it.

I have looked into hard money loans but they are all for investors.

Figure and NYFTY are easy automated HELOC programs with super quick closings (I did one for a client that funded in like 72 hours from loan app). 

If you are considering working with them, I strongly advise you to double-check the provided rates and terms carefully.During my loan process, I discovered that they had added a yield spread interest without informing me.