Jason,
I`ve made the "leap" from a real job to self-unemployment before. It is a gut-check for sure. I had some rough patches, but never looked back.
For me, the trigger to jump was a situation at work where I was about to be committed to a two year project and I didn`t want to leave my employer high and dry when I did walk, so I bowed out on the front end, pissed everyone off when I did and by the reactions I got, knew then that I made the right decision. And I didn`t have 1 year in the bank.
Actually did it a second time when I got out of the technology consulting business to build my high-tech, alternative materials/energy homes. I tried to spin up the construction company while I ran the consulting operations, but I found that I couldn`t do get the new business off the ground with part-time effort.
If you find that you cannot effectively operate your new business on a part-time basis, then do the gut-check and go/no-go.
As far as your request for " low cost, high quality health insurance provider for small businesses", these are all subjective terms. In my experience, the answer is none, however a good provider is Blue-Cross/Blue-Shield. You will pay a price for their coverage, but it is one of the best in the business.
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Burnin` Green, the only way to go.