House hacking is financially a no-brainer and no city in the US (including Chicago) has more duplexes than Milwaukee.

My wife and I purchased a home at the very beginning of 2022 and "house-hacked."

We would buy this house all cash. 

I'm from Leesburg, and I can tell you—multi-family is a solid choice (piggybacking the previous comments which I agree 💯), especially with that live-in/rent-out, house hack strategy.

I'm having a very hard time with them and on the verge of losing my earnest money on a house purchased to flip.

Quote from @Scott MacComb: I am doing my first true house flip (have remodeled plenty of houses for rental) and am trying to figure out a contract to use with a new general contractor whom I have not worked with previously. 

Hurricane Milton recently caused widespread flooding, yet this house remained unaffected.

I found an area I felt comfortable living in and I bought a house with an FHA loan.

Hence spec house.  

It's an acreage property near the lake that has a main house (2/1), guest house (3/2), and small studio-layout unit (3 units on same property).