Has anyone been in this situation or had a tenant utilizing financial assistance such as Leaven?

A full analysis should include (And you may be on your $100k estimate) holding costs such as Interest, Taxes, Insurance, Utilities, etc.

Make sure any utilities that could be tied to the house (eg water) are paid. 

MY QUESTION to the forum is, my goal is to start another hearing practice outside my county (since I now have a non-compete with the practice I sold) but want to utilize my new real estate license in order to have better access to find investment properties.

The biggest problem is the land needs to be able to be connected to utilities so you can't just buy land in the middle of nowhere and stick a house on it, permits are also a concern but that varies a lot by location. 

Temporary lowering your rent does not affect your ability to raise them later.Empty units provide no income and you are paying utilities, just be sure to hold your rental criteria high.

Tenant currently pays 1350/month. landlord pays utilities.

I utilized a VA loan because I didn’t have enough money saved up at the time to purchase when i found this home. 

Make sure you are comfortable paying the mortgage and utilities for 2-3 months at any time just in case.

The city and utility providers were the only real hurdle.