I would love to continue to flip houses but now having two little boys makes the "live-in" part a little difficult.Outside of real estate and taxes, I enjoy spending time with my family, whether at the beach or in the backyard, and sharing new experiences with my 2 sons. 

I just get my lists fir free from the municipalities:- Most delinquent tax payers- Tax-exempt property owners- Tax-deeded previous owners still in the redemption period- Fire-damaged etc

I am confused on what you are asking, I assume he is 20% owner of the LLC in which owns property #1.If you want to buy a 2nd property without him, simply buy it under a different LLC.

**Realistic Timeline**: I can realistically pay off the house in a year, which gives me a debt-free asset to leverage later.3.

We dont have any section 8 houses in Beachwood but in Shaker we have seen closer to 1650 (owner pays water and sewer). 

Scenario 2 is technically not house hacking, right?

If I buy these lots—7,500 square feet with a 50’ width—how comfortable can I be that the person who buys them from me will be allowed to build a house on them?

My oldest child is going to college next year in a town where I could buy a house for $160k.

In 7 years we will sell our house.  

Consider housing hacking after your first year in college.