Sec. 105(b) Plans for S Corporations and LLCs
I think the main things are to have a written plan... and then to be non-discriminatory...
There are some tricks in how you do this, as I recall. But basically the same rules that apply to pensions (I think!) apply to Sec. 105(b) plans.
And, yes, your plan would be that you give each employee $300 a month or whatever for healthcare including insurance. For regular employees, this would be a tax-free fringe benefit. For you shareholder-employees, the treatment is a little murkier... but probably you treat it like self-employed health insurance premiums. The IRS's first notice of 2008 (2008-01) talks about S corporations and health insurance for shareholder-employees.
Steve Nelson, Publisher, www dot llcsexplained dot com and www dot fasteasyincorporationkits dot com.