We (DotSpots) are distributed and I'm up in Calgary, Alberta. Works well for the two of us up in Canada. It let me cofound the company and work for a while with no salary for some time without having to worry about my family's health.
Unfortunately it doesn't help much when hiring from the USA - the majority of our company is scattered around the states.
This is off topic but ARG. If you are in canada do not work without paying yourself a salary! If you have any investment rather pay yourself salary and claim 60-80% of your salary back under SR&EDs. Much better use of your money and you can even reinvest the money you took out if you absolutely have to (after deducting income tax that is).
Totally Irrelevant, but I come from both these places. Born in Calgary, recently moved to Vancouver. My nascent startup (Matygo) has yet to consider anything along the lines of health and dental etc.
Just curious, but understand if you don't want to share, is your "pre-existing condition" diabetes?
I know two people with Type 1 Diabetes that are basically stuck in their jobs due to their insurance situation. One has a PhD and works in a University lab, which he enjoys, except he had to turn down the opportunity to join a startup because it would've been financially impossible for him.
My pre-existing conditions are the #1 reason scaring me to start a business in the US.
Starting a business in the US is overall a lot easier than in Europe, but the advantage would be even greater if entrepreneurs wouldn't have to worry about health coverage.
It's easy: Just open an office in Canada.
For what it's worth, "pre-existing medical condition" is the #1 reason why Tarsnap is not a YC company.