What I is do is

A. not pay any real attention to the flex contribution when it comes out (well, it does show in Quicken for me)
B. when I pay a bill, I take it out of medical sinking funds
C. when I get reimbursed, it goes back into medical sinking funds.

I like having a bit of a buffer in my medical sinking funds (but we’re on Baby Step 7 so I’m not trying to pay off bills).

It’s totally worth while and anyone with predictable expenses should do it

you save the taxes AND it may lower your tax bracket! Suppose I have $2000 in medical bills. Most of my income is taxed at 25%, so it takes $2.666 of income to pay that $2000 in bills. If I put the $2000 in the FSA, it’s tax-free, so I pay $2000 of bills with $2000 in income, and I get to keep $648, minus taxes, or $499. So putting $2000 in the FSA gets me best online payday loans almost $500 more cash in my pocket. PLUS, my income is lowered by $2000, which helps keep the next tax bracket farther away. (although personally since I file Head of Household, that’s too big a range to move out of either way)

I have a child who will be entering 2nd grade this year

and I agree, this is definitely raising the bar rather high. With that being said, my children (who will be entering first and second grades this Fall) were both sent home the last day of school with daily homework assignments they are expected to do over the summer. They are to turn these in the first day of class when they return in September. They are also expected to continue to work on their Math studies with the online IXL Math tests this summer as well. Lastly, my second grader should have read 600 minutes of reading this fall, and my first grader, 300 minutes. We’re doing a lot of school work over the summer.

I also come from low income and poorly educated in both sets of grandparents

My dad broke the cycle and ended up with a ph.d, but that was without any support. He was punished at home if he was caught doing homework because his father believed that school was a waste of time. My dad stayed after school, thanks to a great teacher that believed in him, and would quickly do his homework before he got home. This teacher helped him get a scholarship – a full ride – but his father made him turn it down. He was forced to work and give his money to his dad. Finally, he left home and worked until he joined the air force. The air force saved him. They noticed how smart he was and encouraged him to take classes. Unfortunately, he missed the time period for them to pay for his school. He worked his way through by taking 21 hard (electronics engineer major) credits every semester. He finally finished his doctorate after he was married with 2 kids.

Once he graduated, he paid for his youngest sister to attend college. Many of his siblings dropped out, but they regret it. His sister finished because she ran away as a teenager and my dad agreed to pay one of his brothers some money so that he could afford to let her stay with them. Their condition was that she had to finish high school. She did and then finished college as pre-med. she started medical school, but dropped out to get married.

But priorities are different. Instead of helping with college, my uncles paid for brand new cars for their kids at age 16. My dad had planned on helping with college for us, but he was laid off for several years. They had a large emergency fund as well as investments that carried them for a while, but my sibs and I decided that it was better for us to figure it out ourselves.

Looking back, I wish that I had taken out less in loans. I hope to make sure that my kids do not make that mistake. They have a college fund each that was set up by their other grandfather. They are still young so I hope that there is time.