One is the market growing, what kind of natural things will I have to deal with (Hail, Hurricanes, Tornados, Politicians), would I want to live there.

Goal is to get a multi-family unit, not have to own a car, and be a (max) 20 min uber ride away from Fenway or Cambridge. 

There are areas in Illinois that are more business owner (landlord) friendly and less friendly to people that want free rides.  

That said, if you stay for two years, I am willing to bet you will ride an appreciation wave too making your return thicker.Here is the trade off, if you rehab flip while living there, it will take long and you need to stay for longer if you want the tax advantages so you can only flip one per year or two.

If you don’t have any negative reviews from this instance, I would keep the listing and let it ride.

It's been a fun ride, that's for sure.

There are so many things that you can do to get started so just remember to take your time and enjoy the ride.

Remember, the wisdom of Real Estate Investing is understanding the balance between when to ride out a great asset or when to cash out. 

This is going to be an exciting ride.

I’d say while you’re educating yourself ride/bike/walk your neighborhood and start looking for houses you could flip.