Best approach to house hacking

[Whitney Patterson]

Hi there! I am new to real estate investing, and I'm beginning classes toward agent licensure in June. Being that I work in education, and I am starting from nothing (with some shared debt), I am looking at a house hack. I currently live in/own a property that would fairly easily split into two units (upstairs and downstairs), and is located in an historic area close to hospitals, restaurants and amenities. Renting the upstairs as a MTR or STR would cover the mortgage of the property. Renting both units could probably cash flow around $1000 per month. Other STRs in the area of smaller size have reported earning potential up to $3k per month. My question is this: Should we move out to maximize cash flow on this property? At what point will I know when we are ready to purchase the next house hack? These answers may seem obvious to you all, but remember-- I've never done this before, so it feels like a huge unknown risk.