Over 4 mortgages, the lender will require six months of “reserves,” the principal, interest, taxes and insurance, plus HOA fees for each house.  

Hi BenjaminYou didn't actually mention if this is a flip or your principal residence.

I am in the process of writing my operating agreement for my LLC in Florida and am naming myself the “Principal” rather than CEO or President. 

You will also be building your credit, paying down your principal balance, and you will have a ton of tax deductions to work with.I am very much team House Hack :) Any questions you can PM me.

Our interest rates are between 4.625 and 6.25 and the balances are less than $100k on each property,  so do we work on paying the principal balance down and not have so much interest to write off or try something different? 

On January 1, 2015, you converts the property into your principal residence, where you live until you sell the home on January 1, 2018, for $350,000.

Of that $7k, $3,4k is listed as principal, $2k as interest, there's a little bit of penalty and $1.7k shown as "Other". 

That's a quarterly payment of $2,400 approx. for the quarters I owe the loan, with remaining principal repaid on sale of property.I'm sure there are downsides, I just can't think of them when compared to hard money.

My monthly statements specifically state that extra payments do not get applied to principal unless I specifically tell the bank that's what they are for.

The most conservative thing seems to hold on to the house as we are paying down principal and have options if the market does drop in the future.