Also if you do not have a lease in place than your rental income may not be counting toward your debt to income.

2) When applying for an FHA 203k loan, will I need a cosigner because of the student loan debt or does that not count on my DTI ratio?

Some take what he said and wisely invest whatever they've committed to stocks and bonds in low-cost funds, properly-allocated, while of course being aware of market conditions and not counting on their asset allocations to save them and investing in other assets classes than low-cost index funds, such as real estate, like you are doing.For others, it drives them to a penny-wise, pound-foolish strategy with the entirety of their investment career spent figuring out how to save a few pennies living frugally and making sure their asset allocation is perfect such that they never pursue anything that could make them truly wealthy.  

I'm too heavily invested now to even think of selling and it's looking like i'll be waiting quite a few years to see any returns and just crossing my fingers that the companies don't go insolvent in the meantime.  

@Andy Cross haven't received a response regarding the property management recommendation yet.

At this point rent from both properties should be counting towards income for the third property which of course would need to be a conventional with 20% down (I believe).

To me, if you can count the debt that started 8/21/15, why can't you count the income that started 8/21/15?

You should be able to cross-reference who was notified and what you find during your own search.

After 1 or 2 tax returns of renting a home (I forget how many), part of the rental profit counts as income, so that boosts what you can qualify for.My brother-in-law has bought 3 homes in around 6 years doing this.

Only tell them you will encumber select properties and once LTV drops the cross collateralization goes away along with the recourse.