I'd never heard of it myself but my friend and his family have at least a dozen rental properties out there.

The valuation and market value of a multi family property differs from a single family and you want someone that understands the distinctions if you go that route.

I’m 30 years old, 10 month old son, juggling taking care of the family, property of 21 acres, an old farm house, work, and real estate.

How do you buy a property one day for 40k put nothing into it and sell it for 80 the next day.. some one is getting screwed :)  I get the math I get wrapping the notes my family had a company call CA Wrap we did hundreds of them .. now they were on vacant land as we were in the land bizz and this is much more aligned to the land business than buying homes and selling to owner occs.. 

My starting questions so far are* If zoning allows multi-family, would I need any zoning approvals for a conversion?

@Veronica Mitchell - A little bit of an open-ended question since Chicago is just so massive and has a ridiculous amount of mult-family properties. 

In most single family zoned areas adding a single ADU is not a value add meaning it will not add more value than the hands off cost of the addition.  

Are they family members?

I want to start house hacking maybe with a single family home or duplex.

As it relates to lease end dates I've seen two things work here. 1) You can stagger end dates as mentioned above or 2) you can optimize for summer - this works better for us in areas where you see students or families with school age children moving to align with the summmer months.Separately, this is a great argument against month-to-month leases.