I lived there for a couple years and I met this guy who has bought and managed a ton of property there. 

I'm imagining something more like add a wall, turn a bedroom into a kitchen-living on one side and a formal dining room into a bedroom on the other side, maybe add a half bath in each unit.

If you need the cash flow to live on and it will improve your lifestyle, then go for it.

Additionally, I am beginning to believe you don't live there to be the "house monitor" as this seems to be going on for a time period. 

I currently live in chanhassen but own rentals and have a few flips going in the rochester area.

I currently live Wisconsin and work in Real Estate.

Real estate is easy to get into, but hard to earn a living. 87% of all agents quit within two years because they don't make enough money.

I ask because I hear single section 8 tenants like to have their bf/gf living in with them...Quote from @Rich N.: @Peter GoellerBecause they way Sec8 does it, is that their local Sec8 inspector is suppose to the know the market rate.So, let me clarify this. 

I buy and hold and do short term rentals and mid term rentals.Located in Racine Wisconsin  Hello Gabriel: I also live in Racine County there are some great deals our way and including southern milwaukee county too!   

Hi Anthony, it sounds like you’re in a good position to start building your STR portfolio, especially with no debt, great credit, and rent-free living!