MY QUESTION
What are some surefire steps I can take to 100% get this working?
I would need real instructions, not one liner answers or vague conceptual desc
First install free_tds and required dependencies.
This worked for me, your paths may be different
gem install tiny_tds -- --with-freetds-include=/usr/local/include
--with-freetds-lib=/usr/local/lib
--with-iconv-include=/usr/local/Cellar/libiconv/1.14/include
--with-iconv-lib=/usr/local/Cellar/libiconv/1.14/lib