Better to have a SERIES LLC, with each property in a separate series.  

This may be a better introduction than the coaching program.  

Yale is great for student housing, traveling clinicians, and other cash flow ideas- not the fastest appreciation in the world, but getting better and the Yale impact as a behemoth "institution" isn't going anywhere :) 

Does one have better internet or phone reception? 

Yes, you'll be paying mostly interest rather than principal paydown starting out with the FHA loan hence the better play for you on paper but maybe not on the monthly.It's not too risky so long as you pick your market(s) and do your numbers right.

Considering your long-term goals, multifamily properties may be a better fit due to their potential for diversification, higher income and economies of scale.

How can I structure this deal better to use as vacation home.

The more they sell, the better that split gets.

Others may disagree on that but rents may also increase which will put me in a better position in the future.

I have considered Nashville area...low taxes, more favorable laws, better cash flow and you still get some appreciation.