How to provide health insurance to co-owner?

[Brian Barfoot]

My business partner and I have gotten the ball rolling on our REI business and since I still have a W-2 job with good insurance I feel very happy with the long-term plan. His trouble is that he is a contractor by trade and is stuck in the "too rich to get government insurance, too poor to buy it independently" hole. So here's my questions:

Do any of you provide insurance as an REI company and if so do you buy in/pool with other companies to get a better rate?

What level of scale did you reach before it became a good idea to offer insurance?

Is there some program for small business owners that I might not be aware of that would make it easier for us to get him insurance?

We live in NY which makes things more expensive for nearly everything and I'd imagine the pattern holds for health ins.