I would like to do it in the Chicago area (more-so the Southside where I’m from) or else the surrounding suburbs.I am in the process of currently refinancing my student loans to lower the interest rate.

I was looking for any recommendations of ones you have worked with that have a very good track record -I am looking to have a dialogue with one or two to see if it makes sense particularly in the areas of "C" or lower ranking properties -thanks in advance

- Usually hard money will offer between 7-12% with lower rates offered to those with more experience, better credit, and more capital contributed to the deal.

We only have 2 months of data, and I'm sure November and April are going to be lower as those are traditionally slower periods in the White Mountains.  

When I called the gas and electric company, they gave me significantly lower numbers.

Which was always 15% lower than what they thought.

I'm guessing 100% lower-end rentals in the neighborhood. 

After a month or two, check your credit for free at CreditKarma and when the lower payments show up on your credit report, get ready to apply for your mortgage.The 3rd step is to choose a bank or lender that is Fannie Mae backed because they recently changed the student loan rules to be able to use the lower payments shown on your credit reports as opposed to FHA's 1% rule or brokers that say they have to amortize your loan to calculate DTI.With the lowest possible debt combined with Fannie Mae, at least for now in mid-2018 until the rules change, you should have the best chance at a DTI that can get you into a property. 

Now I'm just getting started and have only looked at 10-20 properties on the MLS thus far, but EVERY single unit is charging rents FAR lower than I ever paid as a renter. 

In your place, I'd probably submit a new offer for 5-10% lower than ypur previous offer, unless your previous offer was a screaming good deal.