They are over 300 years old and have deep pockets which allows us to self fund all our build projects and get better deals and bulk pricing in materials and other services We can pass these savings on to our buyers.

. - not having a strong or deep 'why'.  

He was soooo deep in the red ON PAPER, and didn't know what to do.

Negative cash flow with high HOA fees is a red flag.

I really want to dive deep into real estate and be a learner & just soak up knowledge.

3-Any red flag in our current structure?

You'd need some deep pockets and the nerves to take on something in range of ~$65m in R.E. acquisitions.

We would need to go into a very deep, very bad recession that is housing related for that to happen however so I would not hope for that. 

If the property breaks even, or operates in the red currently, it will only operate deeper in the negative (unless you find a strong ROI like creating more bedrooms, convert a non living space to living space, etc) with another loan. 

 @Puneet Mahi as others have stated, I would do a deep dive on the markets inside each state to determine where you could have an advantage AND where your family would like to live.