E Equity, how much of the home will you own on day one.  

In the long run, I want to have properties that are producing strong cash flow (eventually would love to own small apartment buildings and syndicate larger deals), but it seems that focusing on cash flow and reinvesting those cash flows will be a slower process than focusing on properties prime for appreciation or with opportunities for forced appreciation.

It’s definitely exciting to see suburban Chicago getting recognition as a hot rental market—it’s something I’ve noticed in my own experience as well.

However, as the saying goes, while everyone is entitled to their own opinion, nobody is entitled to their own facts (as there is only one set of facts). 

Long-distance investing can definitely be a good way to find better cash flow, but it comes with its own challenges, especially for a first-time investor.

Do you own your primary residence?

Not my opinion, this is coming from YOUR own data.I am not saying that softwares are bad.

The PM company needs to issue their own 1099s to the owners. 

I started with a house hack then purchased my own rentals/BRRRRs and now I own a successful 7-figure rental portfolio.

Your plan can be something rough like: I own a piece of vacant land at (address), and I'm looking to rezone it from (current designation) to (new designation) in order to build a new construction duplex which will consist of  2 condos for sale, or 2 aparment rentals, eg.