But after a phone call with Dave, he helped me realize that I could simply sell all four properties in two LLCs at once as a portfolio, and then we can trade everything up at once in a single 1031 exchange.Why does this matter? 

There is always a trade off. 

For 1% rule you can do Brighton Park, Mckinley Park (harder and harder now there), Belmont Craigin, Bronzeville hard to find and super hot right now but pop up once in a while and then there is of course chicago suburbs (higher taxes in suburbs but higher % ratio of cashflow so some trade offs). 99% of deals aren't good.

After doing a live in flip in our first home, and remodeling our second home before moving in, I realized I had a strong skill set and the resources that would be beneficial for flipping homes.

Most of the time these investors are trading off some cashflow for lower maintenance requirements and a higher end tenant class. 

First, should I trade in a car now before we buy a new house?

final numbersour total all in $67,448total profit after we paid the agent 3% and other fees was $21,018.54we split 50/50.lessons learned:you definitely find out alot about someones skills when you work with them. 

I've considered using my Spanish skills to cater to the Spanish-speaking market niche, particularly investors, renovators, or even retail buyers/sellers.  

Joseph While $120K is certainly headed in the right direction, there's no need to guess here.If you have access to the property, which I assume is vacant due to the mold, you should be able to have a skilled contractor go through and identify all the problem areas and the cost to address each of them.

So my activities clearly generate passive income, but at the same time my activities qualify me as conducting a 162  trade or business so I can claim 199A benefits (all my properties generate positive taxable income).I don't issue 1099s to my PMs as they are corporations, and it's my understanding 1099 reporting is not required in that case.