I have two friends who own rental properties and they are successful with their properties, I read Rich Dad Poor Dad twice along with Rental Property Investing and Power of Habit, I've been told by multiple people apart of the Baby Boomer and Generation X that they wish they invested in Real Estate at my age, I was a Resident Advisor at my University and I enjoyed that role so some of the skills are transferrable, and lastly this is the best time for me to take a risk.

If you are retirement age, you can do asset based withdraws from "work related funds" (IRAs/401ks...).

I reside in Massachusetts and have recently taken on the role of landlord for my parents' house as they have aged.

The average age of first time buyers now is 56 years old. 

I don't have any restrictions on pets with the exception of 2 things: no dogs under the age of 1, and breeds listed on my insurance policy that are not accepted. 

Some lenders looks at age of the company and revenue (e.g. business line of credits) hence single LLC may be easier.

That's a great start to your journey at your age, so congratulations.

My goal is to do this for all my 4 younger brothers once they become of age. 

Personally, now that I’m middle aged the thought of continuing to share my living space with roommates has lost its appeal.

Inspection revealed A LOT more problems than we ever imagined a house of this young age would have.