In addition to Cleveland, OH, I would recommend looking into Columbus, OH as well!

I have a roommate in my unit as well, I currently receive $1650 in monthly rent and will be around $2200 when I move and it's fully rented.

Somerville - most areas in that town will rent well and if you can find something in Davis Sq that's the most ideal.

If you have financing on a property and you sell it on a wrap, everything works well until the lender calls the note due.Since you have sold the property, you no longer own it, you can not refinance to pay off your lender.

Well which state?

Also could combine horse boarding as I have room for several horses as well.

Due to the population growth of the last 10-15 years, there are uneven student populations in schools.

So, check your sales contract and speak to a good lawyer as well as your real estate agent if there is enough "damages" to be worth the hassle. 

Study your market and your competition and try to do as well or even better.I hope this helps and wish you the best in this exciting adventure.

I've lived here my whole life and I'm in and out of properties every single day so I know the market here very well.