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Has anyone tried just hiring a specialized accountant instead of dealing with this themselves? I'm in a similar situation (Portugal resident, paying health insurance in UK) and finding it impossible to get straight answers from either tax authority.
I did that last year - hired a cross-border tax specialist for my France/Luxembourg situation. It cost about ā¬400 but saved me nearly ā¬2,800 in properly claimed deductions. Make sure you find someone who specializes in BOTH countries though, not just a general "international tax expert.
That's helpful, thanks! ā¬400 sounds reasonable for the peace of mind. Did you find them locally or use an online service? I'm having trouble finding someone who knows both Portuguese and UK tax systems.
Don't forget about SOCIAL SECURITY TREATIES which are different from tax treaties! In my case (Finnish working in Estonia), I couldn't deduct my Estonian health insurance on my Finnish taxes directly, but I could get a certificate of coverage from Estonia that prevented me from having to pay duplicative premiums in Finland. Sometimes the solution isn't getting a deduction for foreign premiums but rather getting an exemption from having to pay them twice. Worth looking into this angle too!
I've been doing my taxes with a combo of gig work and regular W-2 for years. Here's my take: If your side hustle stuff is pretty straightforward (like driving or selling things online), TurboTax Self-Employed will do the job fine. Just track your income from TikTok Shop in a spreadsheet if you don't get a 1099. BUT if you have more complicated situations - like home office deductions, inventory, depreciation, etc. - paying a CPA for the first year can be worth it. They'll set you up with a good system and you can probably do it yourself after that. Whatever you do, DON'T use the free or basic versions of tax software. They'll let you start the process and then hit you with "you need to upgrade" once you get to the self-employment forms.
Any recommendations for tracking apps? I have like 5 different side hustles and keeping track of everything is a nightmare.
I've had good results with QuickBooks Self-Employed for tracking throughout the year. It connects to your bank accounts and credit cards, then automatically categorizes expenses. You can also use it to track mileage if you drive for any gigs. It's about $15/month but honestly saves me hours of headaches at tax time. If you want something free, a simple Google Sheet works too - just be disciplined about entering your income and expenses regularly. The key is separating business vs. personal spending, which gets messy fast if you're not tracking consistently.
Don't forget about quarterly estimated tax payments if you're making decent money from your side gigs! I learned this the hard way last year and got hit with a penalty because I didn't know I needed to pay throughout the year.
How much do you need to make before you have to do the quarterly payments? I make maybe $800-1000 a month from my side gig.
4 Have you tried going to your former employer in person? Sometimes physically showing up at HR is the only way to get past the ignored calls. Just be polite but persistent. They're legally required to provide your W2. Also, most payroll systems now offer digital W2s. Check if your former employer uses ADP, Paychex, Workday or something similar - you might be able to create/login to an account and download it yourself.
12 This worked for me! My ex-employer was ignoring my calls about a missing 1099, but when I showed up in person they printed me a new one on the spot. Sometimes the old-school approach works best.
4 Showing up in person definitely cuts through the bureaucracy. Most HR departments are overwhelmed this time of year but they'll prioritize someone standing right in front of them. As for digital systems, that's absolutely right. Many companies use these platforms, and employees retain access even after leaving. The login credentials should still work, and you can usually download W2s from the past few years. It's worth checking your email for any registration information you might have received when you started working there.
11 Your ex is 100% committing a federal crime by opening your mail. Mail tampering is taken seriously by the USPS Postal Inspection Service. You could file a complaint at https://www.uspis.gov/report. But honestly, the fastest solution is probably just getting the W2 info directly from the IRS with a wage transcript rather than going down the ex drama route.
Have you considered doing it yourself with tax software? I have two rental properties and some basic investments, and I use TurboTax Premier. It costs me about $150 including state filing, and it walks you through everything step-by-step. The rental property section is actually pretty comprehensive. For crypto, you can import transactions directly from most exchanges or use a service like CoinTracker to generate the tax forms and then import them to TurboTax. Might save you $800+ if you're comfortable with it.
I've tried using tax software in previous years but always worried I was missing deductions. How confident are you that you're not leaving money on the table compared to what a CPA might find? Also, how much time do you typically spend doing it yourself?
I spend about 4-5 hours total, spread over a weekend. The first year took longer (maybe 8 hours), but now I just update the same information each year, which is much faster. As for confidence in not missing deductions, the software asks you a ton of questions designed to catch all potential deductions. I also read tax articles throughout the year and make notes of anything that might apply to me. I did have a CPA do my taxes one year as a comparison, and they found one additional deduction worth about $200, but charged me $800, so I actually came out ahead doing it myself.
That price isn't out of line for what you described. I pay $1200 for similar situation - personal plus 2 rental properties and some stock transactions. I shopped around and found prices from $800-1500 for similar services. What I suggest is asking exactly what you're getting for that fee. Some questions to ask: - Does it include unlimited questions throughout the year? - Will they represent you in case of audit? - Do they provide mid-year tax planning? - Will they help with estimated tax payments?
This is super helpful! I never thought to ask about those additional services. My CPA charges $900 but includes audit protection and quarterly check-ins, which now seems like a pretty good deal.
Julia Hall
Make sure you're also checking your state tax situation if you moved between states! I moved from Ohio to Pennsylvania last year and had to file partial-year returns in both states. The local city taxes were actually easier to deal with than the state portion.
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Sofia Price
ā¢Thankfully I stayed in the same state, just moved to a different city. But good point about checking state taxes for anyone who crosses state lines! Did your employer automatically split the state tax withholding correctly on your W2?
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Julia Hall
ā¢My employer did split the state withholding correctly, but they messed up the calculation slightly. They withheld at the Ohio rate for too long after I moved to Pennsylvania. I ended up owing a bit to Pennsylvania and getting a slightly larger refund from Ohio. The key is to check the withholding amounts against what you actually owed in each state based on your income during the time you lived there. If you worked remotely at all, it gets even more complicated because some states try to tax you based on where the work was performed while others go by your residence.
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Arjun Patel
Just a tip from someone who processes payroll - make sure your employer has your correct address now! Often when people move, they update their address for W2 purposes but forget to update their local tax jurisdiction with payroll. This can mess up your withholding for next year. Double check your first pay stub of 2025 to make sure they're withholding for the correct city.
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Jade Lopez
ā¢This is such important advice! My husband didn't notify his employer when we moved last year and they kept withholding taxes for our old city. Created a huge headache at tax time.
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