I live right in Glastonbury and I serve the greater Hartford area.

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

Additionally, I am beginning to believe you don't live there to be the "house monitor" as this seems to be going on for a time period. 

Real estate is easy to get into, but hard to earn a living. 87% of all agents quit within two years because they don't make enough money.

I lived there for a couple years and I met this guy who has bought and managed a ton of property there. 

I live in Nashville, TN.

We are planning to purchase a home and convert it into a community living space for people in recovery.

I live OOS and have been doing deals in the Cleveland markets for many years.

I did 7 deals last year from out of state living in Austin Texas.

Buy and Hold investing is a great avenue to begin with as most people live their lives off of residual income.