I know in Connecticut there is a cap on what you can charge for total move in money (deposit + first months rent) based on the age of the occupant. 

The property looks to be in pretty good shape considering its age, but I don’t have much construction/real estate experience and don’t know what I don’t know.

BRRRR is a new term for an age old strategy of adding value and rolling into the next one. 

Furthermore, I Iike the age of the duplexes.

Lastly, as motivation, gary vaynerchuck said that even at the age of thirty you still have your entire life ahead of you, so don’t overthink your current situation you’ll be just fine.

I don't know if the 2 structures is a gift or a curse given the ages of them. 

Real estate training now in this age is everywhere. 

It seems like a lot of work but, in the Internet Age today, the information is at the tip of your fingers.

As Account Closed mentioned the tenants being 55 plus tend to be very easy on the property.Single-family without any age restriction tends to see a little higher demand, makes sense since 100% of the market fits the bucket.

For less than 6 properties, I estimate my big item expenses (roof, water heater, paint, carpet or floors) taking consideration the age of each times that commonly required replacement.