I survived yet another year of self-inflicted tax prep

The annual exercise in accounting self-abuse that is me doing my own taxes ended three months later than originally scheduled and yet still on time, thanks to the IRS pushing Tax Day back to July 15 to make up for the coronavirus ruining everything.

That delay taught me what I’d needed all along to make this math masochism easier: a dress rehearsal a month and a half before the real deadline. Here, my thanks must go to the Virginia Department of Taxation, which extended the deadline to pay state taxes but only by a month–from May 1 to June 1–and left in place the automatic six-month extension to file state returns.

I didn’t want to send too much or too little money to Richmond, so I needed to get our federal taxes close enough to done for me to plug the relevant figures into our Virginia return and get a reliable estimate. I plowed through TurboTax, as usual needing much more time to calculate my business profit after expenses than for any other part of the return. As much as I miss having itemized deductions make a large amount of our tax bill vanish, getting them right did eat up a lot of hours.

(Side rant: My TurboTax labors also went faster than usual because I finally figured out the freakshow workaround required to import statements from some old American Funds holdings. Without that, I would have had to type in those figures by hand because the PDF download this inept investment firm provided was a giant image without any selectable numbers.)

That work yielded nearly-final figures for the federal return that I could flow into a Virginia return in TurboTax. Then I double-checked that result by redoing the state math in Intuit’s woeful Free Fillable Forms online app, what I actually use to file because I refuse to reward Intuit for its rent-seeking strategy of getting states to retire their own online-filing tools.

In past years, TurboTax and Free Fillable Forms have agreed on what I’d owe Richmond or what Richmond owed us. This year, the stone tablet of spreadsheets said we’d owe $10 more than what TurboTax estimated for our Virginia bill. I ignored that at the end of June but went back through all the numbers again this week without finding any reason for the difference. Which is fine–maybe we paid Virginia a Hamilton we don’t owe, but I’m sure my state could use the help these days.

After going over our federal returns one last time Wednesday night, I had them e-filed before 10 p.m. Wednesday, then had the state returns dispatched an hour later. That left one last tax-prep chore: tweaking the Google Docs freelance expenses spreadsheet template that I shared here two winters ago to make it a little clearer which home-office expenses should be added together.