Purchase price: $325,000 Cash invested: $48,750 Purchased a single family fixer upper with the intent to convert it into a multi-family unit by re-zoning the property to include an accessory apartment for the duration of our occupancy.

Find a house with an accessory unit. 

Accessory Dwelling Units will soon become legal in Chicago.

-Buy a SFR and do what is called an ADU - More on that later, or Google it - Accessory Dwelling Unit.

I'm purchasing a home in Montgomery County, Maryland with a licensed accessory dwelling. 

If you build two accessory dwelling units on a single family home, that does not a triplex make. 

Also curious because Im buying my first property to house hack and I want to be sure I know what I can and can't do on the land as far as Accessory Dwelling Units go. 

If you refinanced out you could use your FHA again otherwise Another option may be a single family with a legal accessory apartment / ADU or a single family with mother in law while owner occupied. 

DADU's - detached accessory dwelling units, corner lots, etc.) in specific neighborhoods that you can do to find STR's, build options or long term rentals.

@Aaron FurrIt really depends on your market, 1 bed/1 bath typically are less desirable, having that second bedroom opens up more options as far as people who can rent the space.In my market better solutions are converting a garage to an efficiency or a 1 bedroom or building an accessory dwelling unit.