I was able to travel down and see the property just before closing. 

Make sure you file the lawsuit in your jurisdiction so she has to travel.  

I would like to convert the garage into a one bedroom and rent either to another long term tenant or mid term (30 day min for professors or traveling nurses). 

Also, if you're working with a local bank, theyre likely choosing not to originate  Conventional loans for investment properties and to only offer commercial loans that they hold on their balance sheet, which are subject to their own internal credit policies.

You even graduated from IU so you have access to some awesome loan programs from IUCreditUnion.Keep your job and connections to buy a house, then rent out rooms to traveling nurses. 

My goal is to create generational wealth for my family and to eventually have the financial freedom to say "yes" to travel adventures as a family.

Much of the travel to Maui is international.

The final pro for Omaha that I'll list, is that our Airfield (Eppley) is now in the process of adding an international expansion-- making it an even more attractive place to be that is centrally located, affordable, and primed for continued growth!

A majority of our MTR tenants are traveling healthcare professionals, many of whom are associated with Aya Healthcare. 

MAYBE, if you live in the town, and are VERY handy, and open an appliance, hvac, roofing company and are willing to travel to the 30 closest cities (since you won’t be profitable even if you get all the business in a city that size.) then maybe you’d do ok.