Hey folks,
I’ve spent the last few weeks finishing this up, and I just wanted to report back here with an update (no big surprises, but just wanted to share the conclusion in case this experience is useful for anyone else).
First, I SUPER appreciate all the help, especially bobsmom101’s DMs with more info and worksheets.
Here’s what I ended up doing:
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First, I tried a few online self-fillable forms. They were very similar to bobsmom101’s worksheets, so I opted just to use them instead of manually running the numbers in a PDF. I tried a few different services and they all had their pros and cons, but I ended up filling it out (but not submitting it yet) with HRBlock’s online option. This is what got me the initial ~$5000 number, which is in line with this self-employment tax estimator (i.e., I’m not sure why it’s higher than bobsmom101’s $3k estimate… maybe self-employment taxes? but in any case, it’s close enough to be realistic)
I was hoping using their online self-serve form would make it easier for a real HR Block person to finish my work later in a real office if needed (more on that later), but alas, their online and in-office systems aren’t actually compatible =/
The online self-serve option would’ve cost about $150 to submit to HRBlock (depending on discount code and such), and another $80 or so for an optional online review by a tax professional (of unspecified licensing).
I did not up end up submitting it (even though it was fully filled out), because I wasn’t quite sure of the correctness of my work – especially the various deductions, both depreciable and not. For peace of mind, this being my first time, I decided to find a professional to double-check my work just in case, only for this first year.
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I then tried to find a free TaxAide / VITA person in my area, but there aren’t that many, and the orgs that were hosting them didn’t have any openings quite yet (in mid-January). Because there was a timeliness component to this (my employer was waiting for me to decide what to do for the 2025 tax year), I decided to find a paid tax professional instead, just to get it done sooner. And besides, it’s another business expense I can write off for this year.
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I then reached out to an EA (enrolled agent, per above) near me. She was nice on the phone and said she could help, but after I emailed her my details, she never wrote back. I followed up a few more times by email and phone, but never heard back from her. She just ghosted me
Not sure why… -
In exasperation, I went to the local HRBlock, because they made it easy to find someone with self-employment tax experience (they let you choose the preparer and see their experience/background when you make an appointment). The lady I got had been doing it for twenty years and was very helpful in person, answering all my questions and collecting sufficient details. I had all my invoices and expense receipts ready to give her on the spot.
She had to redo everything from scratch (i.e. the same data I had already entered into the HRBlock online self-serve form could not be accessed and reused by her, unfortunately). She took 2-3 weeks to finish my taxes (vs the one evening it took me to do it myself online).
Her final amount ended up being pretty close to mine (still around 5k), but hers were a little higher. We probably calculated some of the deductions slightly differently, but it was close enough to not really matter. By this point, I was so exhausted by the whole process I didn’t want to sit down and cross-reference every single line item between my work and hers. The end results were close enough, which gave me more confidence in my own initial work.
Her service cost about $500 total (vs the $150-$250 it would’ve cost to do it on my own) and ended up not saving me any money. I willingly paid it this first year, for the peace of mind if nothing else, but I probably wouldn’t do so again.
This year, I probably won’t use a professional again. The self-serve form was actually much quicker and easier than working with HRBlock in person. The step-by-step guidance made it easy to use even for slightly complicated situations like mine (self-employment + brief period of paid employee work + school tuition + business expenses + depreciation schedules… handled all of it with ease). And the final numbers came out really close to what the tax pro came up with.
Online, I could easily pull up all my relevant docs and spreadsheets alongside and copy-paste things as needed. In person, not only could she not reuse my prefilled HRBlock online form, she couldn’t even accept my documents by email or USB drive. She had to get her secretary to print everything out, scan them back in, and manually enter them in by keyboard (I have no idea why). It took me more time to walk her through my details than it took me to actually just self-file it all online with the form. And it was a lot more expensive.
It was worth it this first year just to make sure I did the work OK (it was close enough in the end), but too expensive for future use.
I didn’t have any particular preference for HRBlock’s online software. It was fine… not perfect, but good enough. Some of the others, like TaxAct’s, also seemed fine. I only chose the HRBlock one this year in case I needed to go into an office, but turns out the two systems are completely disconnected anyway, so that didn’t help at all. Most of the online providers do offer the option of a virtual online review, which is still cheaper (and faster) than having a local person do it from scratch.
So that’s that! I just wanted to share my experience in case it helps anyone else. Phew. What a pain. Thankfully, starting in March I’ll be an employee again, and can let someone else worry about all the taxes!