Thank you to @Cel Arrington, @Tyler Daniel Flinchum, @Taylor L., and @Jeremy Hart for being so helpful and sharing your perspectives and experiences! 

If that's your situation, and you feel confident with your analysis and numbers, then I would go for it, as not only will you be getting cash flow, but it will also serve as a great learning opportunity!

Best of luck and nothing will serve you better than relentless hard work.

I am assuming you will take out a loan under your personal names and then quit-claim to an LLC or you may have a commercial loan and buy it under an LLC where you and your partner serve provide personal guarantee. 

Given that you're brand new and will be living on site as well you may be better served to target an empty property.

The goal here is that after the first year they will have established a track record that serves as it's own landlord reference for me to renew without requiring the double deposit.

Does P&L of all properties count as gross income?

There are a l of of markets that will cash flow but if you are looking at a long term buy and hold, a healthy and growing economy is important to future asset values.

I think trying to squeeze as much as possible out of a termination and trying to force a tenant into staying put when they don't want won't really serve you well in the long run. 

Luckily our tenants are of high quality but markets with better cash flow are now on our radar and we will take the icing (Appreciation) when it is served up but only as a luxury.