If yours is usable and if you want to get the benefits and struggle with the mental overhead (like me), the way I solved it might help. I projected the expenses we were almost certain to have (took about a minute.) Then I put a range on the expenses we'd probably have. That's where I set the FSA withdrawals. There was realistically a 0% chance I was going to lose money with the FSA. If gambling stresses you out, just do a conservative amount and be content with the savings from that.
That was 2022. For 2023, FSA planning was easy because I knew I'd be paying for orthodontics, so I just set it at maximum and spent the whole thing up front in January. I'll probably be back to a lower amount next year. It takes a minute to update the withdrawal in our benefits portal during open enrollment.
The ADHD tax is real, and this article calls out its mechanism exactly, though not by this name.
Similarly, my work has two options for commuter benefits. Monthly transit passes or like a $20/mo bike credit. The transit passes process automatically and do not accumulate. The bike credits can in theory accumulate but you need to manually manage these more that, bring receipts, the whole thing. Even though I’m an avid cyclist and spend well more than $20 on my bike related activities every month, the shenanigans around it just make it unusable to me.
If you spend everything in your FSA in January and quit your job, the company has to eat the loss.
(IANAL, blah blah blah)
To guardrail the process, i've integrated my FSA with a small app I wrote as a hobby project that automatically flags eligible transactions. This largely automates the reimbursement procedure, significantly reducing the overhead of manual management and making sure I don't miss much heh.
And in terms of the risk of forfeiture, this conservative approach coupled with the aforementioned automation has safeguarded me against major losses and kept my exposure low. I think the benefits of FSAs are hard to ignore, but they do necessitate a bit more touch than other expenditure vehicles to be sure.
HSAs are a very good tax dodge retirement account, so you should figure them out. Except in California they're supposed to be taxed. Except… HSA providers don't give you the forms you'd need to report HSA investment gains, so it is literally impossible to report them.