I use Mint.com to aggregate our family's transaction data and then manually enter that data into a wonderfully precise* homemade spreadsheet system to track our expenses and help us see where our money is going and how much we can use to save or pay down student loans after each month.
In 2016 there are two added levels of complexity thanks to our decision to go with a HDHP and HSA and to make use of my employer's dependent care reimbursement account. I want to bounce my ideas for how to account for these transactions in my spreadsheet system off of all of you to make sure they make sense.
Health Savings Account
We will use the HSA as a healthcare spending conduit until we have paid off our student loans. Since HSA contributions have the potential to stay in the HSA indefinitely, I will record contributions to the HSA as contributions to savings. When we incur medical expenses I will record them as medical expenses when we pay the bill. I will not record a transaction when I transfer money from the HSA to our checking account to reimburse ourselves, just as I would not record transfers between savings and checking accounts.
Logical?
Dependent Care Reimbursement Account
The dependent care reimbursement account (DCRA) is a use it or lose it account. Therefore, I plan to record the amount my employer withholds from my paycheck as an expense when it is withheld. I will also record payments made to our daycare provider as expenses when the payment is made. When we receive reimbursement from the DCRA, I will record the reimbursement as an adjustment to child-care spending that reduces our child care spending for the period. This is essentially the same way I would account for a purchase and an associated mail-in rebate payment.
Does that make sense?
* My wife would replace "wonderfully precise" with "disturbingly anal-retentive."
