This is a difficult one to answer, as it depends a lot on your lifestyle and buying habits. FSA covers a lot of things you find at the drug store, such as over the counter allergy medicines, cold remedies, prescription copays, eye drops, contact lens solutions, glasses, anti-acids, dental work and much much more. Also, depending on how your company implements it, there could be a wide range of dates for when you can spend the money. I had a plan that was just for the normal Jan-Dec calendar year. Later, it changed so that I could accrue expenses against the previous year's plan until some time in February.

I suggest you try and gather receipts from drug store purchases from the past few months and try and figure out what your average monthly expense is and then multiply it by 12. Add in a the cost of a doctor and dental visit for everyone in the family. Also add in any major planned expenses, such as laser eye surgery, new glasses, etc. Don't forget recurring prescription co-pays such as birth control pills, cholesterol meds, allergy pills or whatever.

This should give you a safe number to use for FSA, as likely someone in the family will end up going to the doctor more than once or some sort of unexpected expense will arise. If you get near the end of the year and have too much money left in your account that you might lose, go on a shopping spree at the drug store and stock up on stuff for the next few months. You can't buy a HUGE quantity of any one item, but it's pretty easy to spend a couple hundred dollars on a variety eligible items to keep you from losing your FSA money.

I suggest not seeking a generic "Family of 4" dollar value, as every family's number will be different. Some years I've used several thousand dollars in a FSA for only two people, and wished I had contributed more. In other years I've had to use year-end drug store buying sprees to use up my $1,500 FSA before I lost it. I don't think I've ever used less than $650/per person in my relatively healthy home, and we often use considerably more.

Since you are new to the program, keep an eye out for drug stores that put a symbol or code on the receipt next to each FSA eligible item. Places that do this (such as CVS Pharmacies) make it really easy for you to keep track of which items are eligible so you know what to get reimbursed for.

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