Or any seasoned investors that could advise on smart steps I could take in this period in life?

There is no easy way out, and a second mortgage to pay student debt is FAR from a smart move in my opinion. 

Is there someone that this community would recommend who could help with establishing a business entity (be it a partnership, LLC or something else I'm not aware of) so that we can buy and sell real estate investments in a smart and careful way?

This guy is too smart and has money.

My question is would it be smart to buy a townhouse or house and that new community and then rent it out?

Smart Move usually provides a recommendation but now it states "Not Enough Information".

Is it a smart idea to sell and then invest into another property to flip or should I refinance and keep the property and buy another one?

If you simply 'must have it', then Mr Masotti's advice sounds excellent (obviously a smart guy with experience).Just my 2 cents.  

Obviously there is more management on my part and more wear and tear, but is this a smart move?

Be smart and protect yourself, screen your tenants thoroughly and provide a quality product and I doubt you will need an attorney anytime soon.