I'd definitely be interested in seeing that code! My Python skills are pretty basic but I can probably figure it out with some examples. Would it work for someone who's not a developer but can follow instructions?

Absolutely! It's actually pretty straightforward, even for Python beginners. The code is about 25 lines and mainly uses the camelot library which does most of the heavy lifting. You just need to install Python (if you don't already have it), then pip install camelot-py and pandas. I'll set up a simple version that works with the standard Workforce Intuit format and share it via DM. It basically loops through a folder of PDFs, extracts the tables, and outputs them to either CSV or Excel. You'll just need to point it to your folder of PDFs by changing one line in the code. I've documented it well with comments so you can see what each part does.

We tried that route and got a flat "no" - they said it was an enterprise-only feature and wanted an extra $5k per year to upgrade our whole account just for that functionality. Total ripoff.

Do most consulting companies actually offer this? I'm a consultant too and had no idea this might be a thing. Is this common for larger firms or just certain industries?

It's definitely more common with mid-to-large consulting firms that specialize in industries where multi-state work is normal (IT, healthcare, engineering). My company (about 500 consultants) started offering it after too many people complained about tax preparation costs. Smaller firms might not, but it never hurts to ask HR. Some companies don't advertise it well - ours is buried in the benefits portal under "lifestyle perks" rather than with the main benefits. Worth checking your company intranet or asking colleagues if they know about any discounts.

Wait can you explain more? I thought state returns are separate from federal? Why would filing them on different platforms cause issues as long as you enter the same W-2 info?

The issue is that your state returns reference information from your federal return (adjusted gross income, deductions, etc.). Each tax software might calculate these numbers slightly differently based on how they interpret certain situations or which deductions they find. For example, if TurboTax calculates your AGI as $58,750 on your federal return (which affects your CA return), but then FreeTaxUSA calculates it as $58,600 when you try to do just your NY return there, you've now reported two different AGIs to different states. States compare notes with the IRS and each other. When they see discrepancies, it raises flags. You'd need to manually ensure every number matches exactly across platforms, which defeats the purpose of using software in the first place.

Wait what?? I had no idea about these state filings. I'm in Michigan - do you know what might be required here? Is this something completely separate from the tax extension stuff?

Michigan requires an Annual Statement for LLCs, due February 15th each year, and there's a $25 filing fee. This is completely separate from your tax extension - it's more about keeping your business registration active with the state. You file it with Michigan's Department of Licensing and Regulatory Affairs (LARA), not with the tax authorities. The good news is that Michigan sends reminder notices, but don't rely solely on those. Missing the filing can result in your LLC being not in "good standing" which could affect your liability protection. You can file it online through Michigan's LARA website. This is definitely something to add to your annual business compliance calendar!

30% seems high though? Doesn't it depend on your profit margins and tax bracket? I've been setting aside about 20% and it's been enough so far for my freelance work.

I tried the import feature but it only pulled in half my transactions for some reason. Did you run into any issues with missing transactions? And did TurboTax detect all your wash sales correctly?

I did actually have that happen on my first attempt! The problem was that my PDF had two pages, and TurboTax only imported the first page. I had to combine all the Stash PDF pages into a single document and then it worked perfectly. As for the wash sales, yes - TurboTax identified them correctly after importing. I double-checked a few transactions manually and everything matched up with what was on my 1099-B. Just make sure when you're reviewing that the "Box A" checkbox is marked for covered securities, since that's what most Stash investments are.

I noticed the same thing! Stash rounds to the nearest cent on tiny fractional purchases, which creates these small discrepancies. If the difference is just a few cents, I wouldn't worry about it. The IRS isn't going to come after you for pennies. But if you're seeing bigger discrepancies, definitely worth investigating.

Thanks for confirming I'm not going crazy! The discrepancies are mostly small - under a dollar for each transaction. I was just worried because there are so many tiny transactions that it might add up. Good to know this is normal with fractional shares and rounding. I'll stop obsessing over the pennies!

This is really helpful advice that I hadn't thought about. With my parents' history of financial abuse, I definitely need this extra protection. Is this something I should do before or after catching up on my back taxes?

I would recommend doing it as soon as possible, independent of catching up on your back taxes. You can request an Identity Protection PIN directly from the IRS website by going to their "Get an IP PIN" tool. This will help secure your tax account immediately, even while you're working on filing your past returns. The IP PIN is valid for one calendar year, so you'll get a new one each year. This ensures that even if someone has your personal information, they cannot file a fraudulent tax return in your name because they won't have the current PIN. Given your history of family identity issues, this extra protection is definitely worth setting up right away.

The Fresh Start program is great but it's mostly for people who've already filed and owe money they can't pay. For unfiled returns, you need to file first, then look into payment options like an Installment Agreement or Offer in Compromise depending on your situation.