I have learned:
1. Access to the FSA account persists past employment. If bills arrive later in the year, that's ok.
2. Service dates of charges must be within the effective period.
3. The effective period ends by default on the last day of employment. Some employers arrange for an alternate end date (ie last day of the month).
4. Burning the money against your insurance deductible is easier said than done. The expensive policy that accompanies eligibility for a healthcare FSA (at least in my case) covers most in network drugs and doctors immediately, with a small copay.
5. FSAStore carries a lot of mediocre, overpriced stuff. Most of it, I'd never pick with "real" money.
6. The benefits administrator was very clear - the full year's contribution is mine to use, prior to leaving the job. I'd even say they encouraged it.
7. Most of the coolest FSA eligible stuff (ie massage, gym membership, etc.) requires a doctor's note.
8. Buying more than 3 of anything triggers stockpiling rules. Don't do it.
9. Pre-paying for services isn't allowed. Our insurance policy wouldn't even allow the doctor to order multiple months of expensive Rx.
10. As others in the thread suggested, new glasses can provide an expense. We use Zenni though, so it only burned a couple hundred dollars.
In the end, because I don't want to stress over substantiation or hassle our doctors, we spent the vast majority at FSAStore. Finding enough wants required reaching out to family. With quitting so early in the year, maxing the account was still a good deal. I'd be pissed if it was my real pre-tax dollars going to FSAStore.
A high deductible plan plus HSA makes far more sense financial sense, if we would have been under employer insurance all year.
There's probably an angle where someone could buy the expensive FSAStore items, then sell them used. Breast pump, stethoscope, wheel chair, etc. Hard to say it'd be worth the hassle, especially during covid times. Maybe donating product would work well, for the more charitable minded.
