Having your license also makes it so much easier to find, see, and analyze properties since you have access to the MLS for pulling comps and getting showing instructions.You may also find that you actually do like working as a realtor on more "traditional" transactions and helping people (both other investors and retail home buyers) buy and sell homes or manage properties, and it can be a great alternative income stream.

We are currently using traditional financing with 20% down.Unit 1 - rent = $495Unit 2 - rent = $650Total income = $1145Cap rate (based on our offer) is 16.4%Cap rate (based on asking price) is still 14% ROI = 34.41%Picture below is from Bigger Pockets calculator:Picture number 2 below is our own calculator at full asking price purchase: if we were to increase rent on the smaller unit our cash flow will increase (easy added value).After walking through the property twice we see no real updates that are needed. ($0 estimated repair costs)We are waiting to hear back from the agent if we need to counter offer.  

Do you have pictures of the house empty, or with more traditional furniture? 

If you want traditional financing from a bank, how to get it would be finish school and find a job before trying to get a loan.

Typically we are focused on a more traditional BRRR approach but this one had a unique potential value proposition that we wanted to explore under contract.

Is it easy to have a positive cash flow assume 20% down with traditional finance?

From that, financing our first deal with traditional loan would not work ( and it did not as I have tried mortgage brokers and a number of them are very specific on W2 requirements).

Third, my primary debt (aside from mortgages) is student loans, which is driving up my DTI to the point where it might preclude obtaining a traditional mortgage.  

I'm not sure if LLCs can get a traditional 30 year fixed mortgage.

If you had used a more "traditional" 25% down mortgage to buy in the Midwest town, would that have worked?