She also received extra money from Illinois Housing for a month I was no longer living there. 

Housing IQ predicts a 9.3% increase in home prices over the next year, with the median sale price expected to rise from the current levels​​.Inventory and SupplyInventory levels have been gradually increasing but remain below demand, maintaining a seller's market.

The value of your house is essentially determined by the opinion of one person.

Instead of selling our house, we have decided to rent it.

It was our first house and me and my wife bought and new it was a great investment that would work with college rentals and younger families.

Our current housing situation is that we are house hacking by house-sitting for our snowbird mom (so we basically have no housing payments), and we are looking to stay that way until we have to move (5-10 years?).

I have recently started diving into the idea of house hacking to start my career in real estate so bear with me...I have no actually plan yet as I'm still learning but I'm gonna run down an idea I have in hopes to gain some knowledge. 

I think some would work well for a Househacker, someone looking to BRRRR, and some are just buy and hold for cashflow plays.

It sounds like you're already in an excellent cashflow position with your current home, so if you can make a second primary work as a house hack, there are also ways to save. 

The house is perfect turn key for STR and Storage rental.