This is least effective way to maximize this deduction.
Another way is to run them is as an employee benefit expense. This will allow you to deduct them in full on your s-corp return; however, you would need to include that same amount in box 1 of your W2 so it would be included in your gross wages.
There are 2 other options that are the BEST way. As an s-corp owner myself I am in a program called BASE, it stands for Benefit Administration for the self-employed. More information can be found at:
www.baseonline.com

You have to join BASE for this to be effective and you can begin deducting your medical expenses the day you join and not sooner. The annual fee is $224. This program allows you to take all of your medical bills OUT of gross wages on your W2 and you do not have to pay Medicare or social security tax on that amount. This is a HUGE savings as you match Medicare and social security since you are the employer and the employee. A small adjustment is made on your W2 at year end after you enter all your bills on the BASE website and they approve them. Basically the IRS code approves this as an approved HRA plan as long as you hire a third party administrator, which is the fee you pay BASE. The fee is a deducible business expense as well. Please contact me to sign up for this program.
The last option is to open an HSA (health savings account). You can do this anytime during the year for the tax year you are wanting to take advantage of it. You need to open this at a bank of your choice and they charge a fee, but the amount you put in the account is a 100% write off on page one of your personal tax return. The amount must be used to pay medical bills.
All of these options are subject to change based on personal circumstances of your own tax situation and you should always seek additional advice before proceeding.

Jennifer A. Harris, President/Owner
Jennifer A. Harris CPA & Associates, Inc.