This is commonly referred to as the BRRRR strategy.If you are looking to grow a portfolio to gain passive income to replace your current income this is a perfect strategy to use.  

Demographically, most of Connecticut isn't growing.

With two going into college, I am driven to grow more income through RE and would like to teach and inspire my daughters about building wealth through RE.

That little books has helped me grow my business into a six figure business in three years. 

I want to use some of the money to help grow my business.

Once your net worth grows it might be worth considering in the future, but for now in my opinion liability insurance + umbrella policy should be sufficient. 

My term is 1st+last + security. 3 times rent of about 900$ is not something ordinary people (not rich but "working") should have?

This would also afford me the security of having around $6K cash flow monthly coming in from my business should I have some unforeseen “bumps in the road” with my rookie real estate investing but also afford me true potential to grow my real estate portfolio.Plan B is to sell my business and use the cash to purchase several multi-unit properties or even an apartment.

Oak was only rarely used in US housing built in the 1900s as framing lumber, for the simple reasons that most varieties of oak don't tend to grow straight, oak grows much slower than most pine species, and oak is usually extremely heavy.

Are there any hot and growing areas to get in now?