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
Well, unfortunately I've now got it working and have NO CLUE how I've done it but I will list all of the things I've done so far in this answer to solve it.
In the end, bundle install
with standard gem 'tiny_tds', '0.5.1'
ended up working fine.
It's running Ruby version 1.9.3-p194 via RVM.
This is where the gold is I'm fairly sure...
I used rvm pkg install iconv
and rvm reinstall 1.9.3 --with-iconv-dir=$rvm_path/usr
Once this completed, I deleted all old gem folders... I switched bundle config path to match the new ruby path...
Then did bundle install, and boom.
It's also using iconv 1.13 instead of 1.14 not sure if that matters.
I hope this helps anyone... it's definitely been a huge learning experience for me.