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Early research indicates that it may be more cost effective for me to put about $350 of that money into a savings account each month against doctor visits and whatnot

If you're in a small business, have you looked into medical savings accounts? You can deposit 65% or 75% of the deductible each year, and use the money for medical expenses. Deposits are tax-deductible and interest is tax-deferred (like a traditional IRA).
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