The first shop I worked at had a group insurance plan, and I'm glad I kept it via COBRA when I changed shops, because I crashed and broke my wrist w/in a month. The second shop had no health insurance for employees.
My brother (also a bike mechanic) and I shared an apartment, I owned my truck outright, we had no cable or other luxuries. We lived off of frozen burritos and ramen.
That was 13 years ago.