Based on your first fix/flip, it sounds as if you don't have any issues doing moderate rehab.

The cash on cash return is only meaningful when you evaluate it based on your long term plans.

I'm sure it was highway robbery - it certainly was based on the man-hours it took - but when you are in a desperate situation, you do what you have to do to get yourself out of it.  

I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.

Without a firm base and working familiarity with these three areas the investor will not have the knowledge to analyze, negotiate and close advantageous real estate transactions. 2- Experience - the first few deals are likely to be smaller, harder, with more “surprises” and not as profitable as the investor imagined.

I am a licensed realtor based in Atlanta, Georgia, and I am currently working on obtaining my mortgage origination license.

I'm an investor and Realtor based in Central NJ. 

Airbnb is very algorithm based and despite the popular opinion its not hard to stay in good standings on the algorithm. 

It's just a pass-through entity so the income would flow on to your personal and you would pay taxes based the tax bracket you fall in for you personal income (from my understanding).

Since you’re based in NY, Detroit is just a short flight away, making it feasible to visit and get a feel for the market and the team you’d be working with.That said, I’ve worked with plenty of investors who have never actually visited and still built successful portfolios—it really comes down to having the right boots on the ground.