The higher initial cash flow market will in general have worse cash flow over a long hold than more expensive markets.  

But as long as its not directly in the flight path, it will be okay. 

I have proof of all of it and we are ready to act swiftly.

It seems like your goal is appreciation or that you are willing to sacrifice cash flow for appreciation, as long as your return is trending in the right direction.

Investors think in numbers, exit strategies, and long-term plays, while homebuyers think in emotion and monthly payments.What are some of the biggest differences you’ve noticed when working with or transitioning into real estate investing?

Option A would allow me to keep it as a long term rental .

However, the opportunity cost is that I won't have funds to invest with my current salary as long as I have this house.

I have 3 long term rentals, but this is my first time with commercial property. 

Hi Brett - local PM here - we have a few development projects, small multifamily and tonwhouses that we are gearing up for sale in the next 6 months.

Some focus purely on numbers, while others look at long-term value, location trends, or creative financing strategies.For those of you investing in Chicago (or similar markets), whats your mindset when evaluating off-market opportunities?