If the interest you're paying your father or someone else, combined with the interest on the mortgage, combined with the principal paydown, the rent received, the expenses... if everything results in cash flow that meets your goals, then it will all come down to mustering the faith to take that next step.I would highly recommend connecting with someone locally who has house hacked... pick their brain, learn how they made it work, etc. 

I have a strong desire to earn money in an entrepreneurial fashion and utilize my skills in new ways.

As of now, I do not have any updates on tenants/applications or a confirmation on pending/remaining repair itemswater (utility) ON?

Looks like I can pick up single family homes for $50k or duplexes for $100k.

Tenants pay all utilities and one of the units is rented for $750.

Not sure what her exact score is, but it could be boosted by paying off her $300 credit card (which has a high utilization at the moment).

Eventually, I will be utilizing the BRRRR method when financing permits.

Most 2 unit properties have similar square footage to each other and have separate utilities and separate addresses. 

The areas where students live have been picked thin by investors for years.

@Wagner AlcivarIf I were you, I'd pick up the phone and try calling other homeowner insurance providers.Allstate, Progressive, State farm, Amica Mutual, etcThere are plenty of them and they each have different underwriting procedures.With some, you'll qualify.