The truth is, you will end up paying more in taxes having that income instead of passive investment income from the LLC or S corp from investments, so I am sure the IRS would be happy to take your money.Keep in mind, when he makes you a W-2 employee, he not only has to pay FICA, medicare, and now with the new healthcare laws, there's that too. 

Health care premiums are not tax deductible.  

I ran into the same dilemma with being self employed and needing insurance..My wife and I were using golden rule which cost about $100 per month for the both of us up until ACA was passed and she was allowed back onto her parents excellent government job healthcare plan.

Why does Bezos continue to work so hard to achieve new heights, why did he buy whole foods, and now healthcare company and blue origin to go out of space?

Not because of the fact of possessing it, but due to the opportunities it gives you - some better life conditions, complete health care, better goods and services, an opportunity to travell, etc.

You want to take advantage of cyclical markets.And where are you going to get affordable healthcare.

But in todays society the healthcare field is highly governed by patient satisfaction almost, if not, more than delivering great healthcare.

Industries such as healthcare, agriculture, oil and energy will be here to stay. 

Finding affordable healthcare under 55 will be the hardest part IMHO. 

We live for $3,000/month in Cuenca, Ecuador sending our kids to private schools, eating great food, buying private health care, drinking local craft beer, and taking excursions around the country. $60,000 to $100,000 per year and you can live like a king/queen here and many other parts of US and the world.And, something many people don't consider is how much less things costs when you have flexibility of time.