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I park seasonally but it looks like I could do $50/mo pretax even if I spend $0 in July and $100 in August since it clearly says not subject to use it or lose it?
The amount you set as pre-tax benefit is the amount that you will not pay federal tax and if state uses federal AGI then no state tax similar to 401k deductions. Since it takes time for it to adjust for payroll, I would recommend to average it out for year and then divide by 24 to get deduction for each pay cycle. Or if you want it to be really accurate, you can adjust it based on last month and keep updating each month on same date.
Yes, you should keep records but since it is small amount I had not kept any records.