I personally like your strategy if the person is not working for an employer.In your case, you have a W-2, therefore, I prolly wouldn't recommend it.One of the benefits with the S-Corp structure is being able to deduct healthcare costs and retirement contributions.However, healthcare costs are likely(hopefully) partially subsidized by your employer with your employer providing some sort of retirement option.Why is your CPA busy now unless he/she is working on foundation tax returns?

We'd like to qualify for a healthcare subsidy and sell a house capital gains free wihle we're testing our early retirement.

TI, McAfee, Intuit, Fossil, Erikson, Raytheon, BCBS, Dell, HP, Tenent Healthcare...I could go on and on, are already there and expanding.  

It's too dangerous otherwise.Mom knows and can have health care professional writing those prescriptions call you and give you definitive answer on medication.

@James HardieMetro Detroit (my rental portfolio is here)Purchase: $80k-$130kRent: $1200-$1500ROI: 10-14%Cash flow: $250-$350/doorAppreciation: Double digit (for past 10 years, will gladly send data)Location: C+, B- (suburbs and certain markets)We have over a dozen Fortune 500 companies just in Metro Detroit with huge Healthcare, Auto, and mortgage industry National footprints.

I have kids in school and currently looking for a part-time day job in health care. 

I graduated Purdue with a degree in construction management and have a few years under my belt as a general contractor in commercial healthcare. 

@Brian Simmons, I understand the reasoning behind sending those kinds of letters to healthcare providers.  

They rely on the government for food, housing, healthcare, transportation, etc.

(I currently make a little over 60/yr)  I still have a casual job and am about to finish my healthcare management degree in June to open more opportunities until I get investing up and lucrative.