Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high.

@Chris Risi Have you looked into advertising for Lead Generation on FB?

Once we find a new (longer-term) home for ourselves, we can then rent out this property and start generating cash flow, leaving us with our first investment property!

Hi, I am a young newbie looking to generate passive income through real estate investing.

Once we find a new (longer-term) home for ourselves, we can then rent out this property and start generating cash flow, leaving us with our first investment property!

I know every available on-market property, have made connections to sources of off market lead generation and its great income. 

@Aaron CarltonI would not have one minute of pause for 2 reasons:Her office is not a Broad listing brokerYou are not considered immediate family as you are a generation removedKeep in mind, there is no penalty even if you were immediate family. 

I would like to start off with a decent size single family home that could generate a quick flip giving me some experience and generate a good profit.

I have a partnership with a nonprofit that allows an investment property to generate around 1.25 to 1.75 times the average rental income in my area.

Responsible leverage builds generational wealth.