I work at a company with around 50 people and we got this set up last year! It's called a Section 132 Qualified Transportation Benefit. Our HR person said it was surprisingly easy to implement through our payroll provider. The company actually saves money too because they don't pay payroll taxes on the amounts we set aside for parking. In my case, I'm saving about $70/month by paying with pre-tax dollars. Definitely worth asking about!

Thanks for sharing your experience! That's really helpful to know. I'll definitely bring this up with our HR person then. Did your company need to hire some special benefits provider or was it really just handled through your regular payroll system?

Some employers also have deals with nearby garages that employees don't know about. I randomly mentioned my parking costs to our office manager and found out we get a corporate rate that's $75 cheaper per month than what I was paying. I'd been overpaying for TWO YEARS because I didn't ask! Might be worth checking with your company.

1 Thanks for the tip about the screenshots! Does it matter if I save them digitally or should I print them out? And I hadn't even thought about state requirements being different. I'm in California - anyone know if they have different rules?

22 Digital records are fine as long as they're organized and accessible if you ever need them. I keep mine in a cloud folder organized by year and vendor just to be safe. California generally follows the federal $600 threshold for 1099-NEC reporting. However, if you're registered with the CA Employment Development Department, they have some specific reporting requirements. The main thing in California is making sure you're properly distinguishing between contractors and employees - they're pretty strict about worker classification with their AB5 law.

10 I use QuickBooks Self-Employed and it's been pretty good for tracking all my freelancer expenses. It connects to your bank/credit card and automatically categorizes most transactions. The nice thing is you can tag Fiverr expenses as "contractor payments via platform" so it's clear they don't need 1099s at tax time.

Is there a threshold for this Spanish filing requirement? I have a very small investment account in Spain (under €1000) and wondering if I need to bother with this.

Yes, there is a threshold, but it's based on your income, not account size. If your Spanish-source income is below about €1,600 annually, you're generally exempt from filing the Modelo 210. However, rules can change and there are exceptions, so it's worth double-checking with a Spanish tax advisor if you're uncertain. When I had a similar situation, I found that even though I wasn't required to file in Spain, having documentation from my Spanish bank about any tax they withheld was crucial for claiming my US foreign tax credit correctly. Ask your bank for an annual tax statement ("certificado fiscal anual") to help with your US filing.

Yes, the US-Spain tax treaty does address capital gains. Generally, under Article 13, capital gains from selling stocks are only taxable in your country of residence. So if you're a US resident, technically only the US should tax these gains. However, Spain might still withhold taxes, and you'd need to use Form 1116 to claim the foreign tax credit. As always with international tax, there are exceptions and complications. For example, if the Spanish company derives most of its value from real estate in Spain, different rules might apply.

Which software are you using? I had the same issue with H&R Block last year but this year it seems fixed. Try entering the acquisition date as 01/01/2021 instead of 1/1/21 - sometimes the date format inconsistency causes problems.

I'm using TaxAct. The weird thing is that it's only happening on some transactions, not all of them. I'll try your suggestion about the acquisition date format! I've been using month/day/year but maybe it needs the leading zeros. It's just so tedious to fix each one when I have about 40 transactions from 12/31/23.

HAHAHA I did the same thing on an email to a client! I typed "As of 123123" instead of today's date. And I keep reading the number on receipts as dates now. Tax season madness is real!

This is such a good point. I live in Washington state so we don't have income tax, but when I moved from Oregon I got a nasty surprise tax bill because I didn't realize how different the systems were.

Exactly! The state differences are huge. I moved from Tennessee (no state income tax) to California (high state income tax) and didn't adjust my savings strategy. Big mistake! Just remember that the general 25-30% rule people mention is usually just for federal taxes and self-employment tax. You need to add your state's rate on top of that.

Do you use any specific apps for tracking? I'm terrible at keeping up with spreadsheets and worried I'll mess it up.