F1ling Season: Box, Box, Box!

This year, I didn't just do my taxes. Oh no, that would be too simple, too straightforward for the likes of a busy dad. I, in my infinite wisdom and with a healthy dose of bad luck, managed to do my taxes twice. Yes, you heard that right. TWICE. My tax journey this year felt less like a Ferrari and more like a Williams. But hey, when life gives you lemons, you make Arnold Palmers...wait, that's not how that goes. Maybe instead you just write a blog post roasting the two main instigators of your pain 😅 So with a recent binge of Drive to Survive in mind, and a recent bout of tax-related rage, let's get crackin'.

The Starting Grid: An Unscheduled Pit Stop

It was late, the kids were finally asleep, and I'm surrounded by a small mountain range of W-2s, 1099s, K-1s, and 990s (don't even get me started on 990-PFs). I'm using H&R Block because, well, why pay 3 separate times for personal, business, and non-profit taxes at TurboTax amirite? (Spoiler alert: I'm wrong!). Anyway, I'm chugging along, feeling like I'm on the final lap. I've navigated the confusing chicanes of deductions, outmaneuvered the tricky hairpins of ESPPs, and I'm heading down the straight, right for the checkered flag, that glorious e-file button.

But then... disaster.

You see, I had decided to make a backup of my return before clicking "review," as any reasonable, cautious person might do. Unfortunately, I had the supremely boneheaded idea to trust H&R Block's backup feature rather than a simple file copy, and, if I haven't foreshadowed enough yet, H&R Block's dev team was not up to the task. Instead of safeguarding my return, clicking backup sent H&R Block careening into the wall in a fiery explosion more spectacular than Grosjean in Bahrain. You see, H&R Block didn't just crash, oh no, that would be far too kind; instead, it wiped out everything. Every meticulously entered number, every painstakingly answered question. Gone. Vanished. Like my hopes and dreams for a relaxing evening, my original save file was overwritten with a zero byte file of nothingness and an atrociously styled red message with just two words: "Backup Failed."

A brief period of mourning (and perhaps some more colorful language) later, I was faced with a choice: give up and let the IRS hunt me down until I succumb to spam robocalls for my backtaxes, or... start over. I chose the latter, with a different piece of software obviously because there was no way on God's green earth I was giving H&R Block another crack at what was left of my sanity.

So, after peeling myself off the ceiling and resisting the urge to throw my laptop out the window (it's a work machine, gotta be responsible), I had a unique, albeit unwanted, opportunity: a head-to-head comparison of two tax prep titans.

Gentlemen, start your engines.

Lap 1: Ease of Use

When it came to just getting around, H&R Block felt, let's say, traditional – less like a friendly guide and more like a slightly interactive PDF. It'll get you there, assuming it doesn't decide to spontaneously combust, but it ain't exactly holding your hand. TurboTax, on the other hand, generally presented a much friendlier face with a more modern UI and clearer guidance, making the whole ordeal feel slightly less mechanical.

Now, the import feature is where both platforms seemed to collectively bin it. H&R Block just flat-out refused to import my Fundrise data, forcing me into manual entry mode. Not to be outdone, TurboTax then choked on my Ally investment imports, leading to more of the same tedious typing. And the cherry on top? Even when an import did successfully slurp in the data, both programs would then insist on manually focusing on every single imported box as needing review. This meant I still had to manually click through and clear everything, completely negating much of the supposed time-saving nature of automatic import. So much for modern convenience, eh? This felt like a new one, so it's possible that this is specific to my tax situation, but nonetheless, it sucked.

Winner: TurboTax

With its slightly less aggravating interface and slightly fewer import issues, TurboTax took this round, but it was a really low bar.

Lap 2: Accuracy

Both services wave their "accuracy guarantees" around like crazy, but let's be honest, those usually just cover basic arithmetic. They don't offer much solace if you misinterpret a question like, "Did you qualify for the Subterranean Domicile Inhabitant Credit under subsection Z, paragraph 3, line item Q, assuming you did not file form 8829-Gamma on a Tuesday four years ago?" I mean, shit Sherlock, that's precisely what I'm paying you to help me figure out! For me, true accuracy means the software guides you to fill things out correctly and makes it easy to understand why.

This is where H&R Block started to feel like it was actively trying to gaslight me. At several points during the process when I reviewed previous sections, it would update my refund amount—sometimes up, sometimes down—when I hadn't changed a single value on the form. I'd just click "next" without changing an answer to a question and suddenly, I'm richer! Or poorer! It was like playing a possessed slot machine with the added threat of jail time for getting it wrong! TurboTax had its own little quirks too though, like initially hiding the input field for Foreign Tax Paid on Ordinary Dividends (box 2f on the 1099-DIV) and getting a bit confused when my K-1 Code V information came as an attached statement instead of a single dollar amount. However, to its credit, both TurboTax and H&R Block did manage to automatically import the foreign tax credit from my 1099-B brokerage statements, so at least there was that.

Winner: TurboTax

Despite some head-scratchers on both sides, TurboTax won this round for not actively changing my refund amount without input changes. Once again, pretty low bar here.

Lap 3: The All-Important Refund

This is where the rubber really meets the road, isn't it? It's all about that final number. TurboTax shone here by catching a crucial cost basis adjustment for my ESPP (Employee Stock Purchase Plan) shares. This is a common pitfall where folks can easily overpay taxes, and TurboTax actually walked me through the adjustment process fairly clearly, which was a relief.

H&R Block, well, not so much. It asked for my Form 3922, which is related to ESPP, but then seemed to just... ignore it? It happily went on to report a gain where, after the correct cost basis adjustment, there was actually a small loss. That's a pretty significant "oops." To be fair, H&R Block did randomly increased my refund for no discernible reason at one point by almost $2000. Thanks, I guess? But that kind of wild inconsistency makes you wonder what other gremlins were lurking in its calculations.

Winner: TurboTax

For actually getting the ESPP details right and inspiring a sliver more confidence, TurboTax clearly took this round. A potentially smaller, but correct, refund is always better than an erroneously inflated one.

Lap 4: Time Savings

My first attempt with TurboTax, before the H&R Block-pocalypse, took roughly three hours, not counting the initial data gathering. This also included the software making me fill out several credit questionnaires it already knew I didn't qualify for based on my W-2 income. Why, TurboTax, why must you torment me so? As if I hadn't already been through enough!

On the other hand, my ill-fated journey with H&R Block actually clocked in at a little less than two hours before it decided to spectacularly implode. Not walking you through a bunch of questions that aren't relevant to you does in fact save you time! Oh, you dufus, you, if you hadn't imploded, you finally would have won a round! But alas, you have failed once again.

Winner: TurboTax

Not imploding and demanding a restart is a low bar, but H&R Block still managed to trip over it.

And the Winner Is... My Desire for a Better System

Overall Winner: TurboTax. It was generally more intuitive, didn't eat my data, and ultimately, guided me through a couple of tricky adjustments to save me real money.

Biggest Loser: Me, for having to do this twice. And, by extension, pretty much everyone in America who has to navigate this yearly gauntlet of confusing forms, questionable software, and the ever-present fear of an IRS audit thanks to incessent lobbying of, you guessed it, TurboTax / Intuit.

So, there you have it. My tale of two tax softwares. It was an adventure I didn't ask for, but hopefully, my pain can be your, well, maybe not gain exactly, but at least your amusement. Now if you'll excuse me, I think I've earned another Arnold Palmer. May your software be stable and your refunds be prompt.