New Member from Chicago has a $$ question about existing rentals

[Vanessa Buccella]

Hi! I'm Vanessa. My husband and I own a home in the north suburbs of Chicago. We both, somewhat inadvertently, fell into owning 2 rental condos in Chicago.  Both of the rentals were ours before we married and bought a house. He decided to keep & rent his as an investment. I couldn't sell mine when we bought our house, so ended up renting it out.  So boom, now we're landlords!

Here's my conundrum: While both of these will (likely) turn out to be a good investment when they're owned owned free and clear, neither are currently making any money right now.  Right now we both deal with our own condos financials. They are each under separate loans, etc. 

We both bought these as our own primary residence, with traditional 30-year mortgages. My condo was with an FHA loan, which I still have. The PMI finally dropped off last September. However with HOA fees, high Chicago Property Taxes and minimal Home owners insurance, what i get in rent barely covers what i pay.

Obviously I have explored 2 choices, re-financing and raising the rent , doing both would be best!. I currently rent it out through a Chicago Section-8 (HUD) program where the city pays a bulk of the rent and the tenant pays the rest. This is nice because the rent is guaranteed to be in my account via direct deposit by the 1st of each month. The drawback is that increasing the rent comes with red-tape and the possibility that the rent will actually be LOWERED, if the market dictates it's too high.

OK so now re-financing: I am a new small business owner. As such my PERSONAL (not family) income isn't that great. My debt to income ratio doesn't look good, on paper. Every time I have spoken with a bank (and i have MULTIPLE times), it's never been profitable for me to refinance, even though i don't have a great interest rate (it's in the 5s). I don't have enough equity and again that debt to income ratio isn't great. 

SOOOOOO ANY IDEAS!? 

PS my condo is more of an up and coming area, my husband's is in a popular area that has a LOT of development right now. We just got new tenants in his. My tenant is now on a month to month. They are both pretty "hands off" as far as tenants go.