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.

I've been using Justworks for my C Corp for about 2 years now. It definitely simplifies the admin side but doesn't really address the tax optimization between multiple income sources. You still need a good accountant for that part. The PEO basically just handles compliance, payroll processing, and can get you better benefits options than you'd have as a tiny company.

This is actually a really good point. I've used fiscal year planning with my S-Corp (mine runs Feb-Jan) and it gives me an extra month to make strategic decisions before the personal tax year ends.

I hadn't thought about the fiscal year angle at all. My C Corp is currently on a calendar year but I'm wondering if it would be worth changing that. Would it complicate my accounting too much to have different fiscal years?

Thanks for this warning. Can I ask how much the penalties ended up being in your case? And did you eventually have to file all the back returns anyway?

The penalties were brutal - about $5,200 for just two years of unfiled S corp returns. They hit you with $435 per month for up to 12 months per unfiled return. And yes, I still had to file all the back returns anyway, plus pay a CPA to help me sort through the mess. The worst part was reconstructing records from years ago. All told it probably cost me close to $8,000 including penalties, professional fees, and state filing costs to clean it all up. Definitely take care of this now while everything is still fresh and you have all your records easily available.

Great point! I was wondering about this because I have the opposite situation - I paid some personal expenses from my business account. How would that be handled on the corporate return?

Wait really? The mileage deduction is that much? I never tracked my miles but I was doing Doordash like 4 nights a week for about 8 months. How would I even calculate that now after so much time has passed?

You can create a reasonable estimate based on your delivery history. Most delivery apps keep a record of your deliveries - try to get that data from Doordash if you can. If that's not possible, make a good faith estimate. Calculate your average deliveries per shift, estimate miles per delivery (including driving to pickup locations), and multiply by your working days. Document how you arrived at this estimate in case of questions. For 4 nights a week for 8 months, you're looking at roughly 128 working days. Even at a conservative 30 miles per shift, that's 3,840 miles or about $2,150 in deductions! Just be honest but thorough - this could significantly reduce what you owe.

Good point about state taxes. One thing to add - some cities also have local income taxes that apply to self-employment income. I found out the hard way after getting a notice from my city tax department a year after dealing with the IRS!

Thanks for sharing your experience from the management side. Do you think I should start reporting my tips to my employer anyway, even though he specifically told us not to? I'm worried about creating conflict but also don't want to be part of something illegal.

I would absolutely start reporting your tips properly despite what your boss says. Create a simple spreadsheet or use a tip tracking app to document everything. Then submit a monthly tip report to your employer (you can find Form 4070 templates online) and keep a copy with proof of submission. If your boss pushes back, you can simply say that you're following IRS requirements to protect yourself. Frame it as something you need to do for your own tax compliance rather than suggesting he's doing something wrong. Most importantly, document everything in case questions arise later. The reality is that the IRS holds both parties responsible, but you can protect yourself by following proper reporting procedures even if your employer doesn't.

Do you have to report credit card tips too? I thought those were automatically tracked since they go through the POS system. My manager only tells us to track cash tips.