Cube, just a thought… I, too, hate all the paperwork and getting “pecked to death by ducks” involved with getting your money back, so I just do it once a year, either when we’ve maxed out the benefit, OR I wait until the last minute to file if we’ve not been able to max it out beforehand. Though you might have to spend an hour or two to get it done, it seems like time better spent when you do it all at once, as opposed to doing it every time you get a medical bill. Personally, I think it’s more efficient.
Also, being very organized really helps. I have one file per year for the FSA, and all of the explanation of benefits (EOBs) go in there, first. As I get the medical bills, I match up the EOB and bill when I pay them, and the stapled (or paper clipped, so they’re easier to scan later) bills/EOBs go in the back of the file. It makes it very easy to quickly calculate which bills I need to submit to get the max benefit, and scanning them into the computer (to send via email) is a snap. I often get just one or two decent-sized checks once a year, which makes managing the checks all that much easier.
