Welcome to the real estate investment game!

I’m curious to hear if people have done this in the past, how they did it, how they started, etc.Any thoughts / discussion / enlightenment on this is encouraged!

I would consider selling one of the properties, paying off the debt, creating a reserve for your remaining investment, and ensuring you are 100% financially stable before you invest again.

Investment Info:Single-family residence buy & hold investment.

Back in the day of my early start I got in "on tour" with Nouveau Riche. 

Quote from @Parker Bullard: I'm looking to purchase my first investment property and need help figuring out a strategy that will work for me.

I think your starting point is off - way off. 

I just need help on finding a path to get my hands on the capital This sounds like an incredible opportunity, especially with your uncle's experience and willingness to help you get started.

I chose to invest most of those gains into a trucking company due to the lack of patience at the time and my 10 year experience being a tractor trailer w-2 driver.

I am starting to get Lynn section 8 folks calling, but I have not gone through the process with them to know how they are with rental amounts.Yes, the ones with sec8 are in Haverhill.