I understand that for a c-corp medical expenses can be considered deductible/business expenses for employees.

I have a c-corp (am the sole employee), and have an s-corp (i have a part time employee <1,000 hours with no medical benefits). I would like the c-corp to cut me a check for all of my medical expenses as part of a "benefits package" to cover deductibles/co-pays/medicine/etc...

Is this possible?
How does one go about setting this up?
An FSA sounds too cumbersome...

Zip Code: 02891

You are correct that while a C-Corp can deduct medical expenses paid on behalf of its owner-employees, and S-Corp cannot.

To do this right, you need to first set up a formal Health Reimbursement Arrangement (HRA) within your C-Corp. You can ask your health insurance agent if they can set one up for you. If they can't help you out, I can point you in the right direction.

You need to be careful if you will be hiring employees down the road. Any benefit you provide to yourself you need to offer to your staff. And since you own 100% of multiple entities, you need to provide benefits to employees of all of your entities. Otherwise, every business owner with staff would set up two entities - one with themselves as the only employee and with great benefits, and the second for their staff with less generous benefits.

Zip Code: 01801