Has anyone considered the implications if OP shows gambling losses instead of profits for several years? The IRS has a "hobby loss rule" where if you show losses for 3 out of 5 consecutive years, they presume it's not a profit-motivated business. Professional gamblers who consistently lose money can have their status challenged.

This is a complex situation that requires careful consideration of multiple factors. While your high W-2 income does shield you from Social Security taxes on gambling profits, you'd still owe Medicare taxes on any net gambling income. The key challenge I see is establishing legitimate business intent while maintaining your tech career. The IRS will scrutinize whether gambling is truly your trade or business versus an investment activity or hobby. Consider these critical points: 1. **Profit motive documentation**: Beyond just keeping records, you'll need to demonstrate a clear business plan, profit targets, and systematic approach to gambling as a revenue-generating activity. 2. **Timing concerns**: Establishing professional status now while employed might actually work in your favor - it shows you're treating this seriously even when you don't "need" the income, which could support genuine business intent. 3. **Risk management**: If you do proceed, consider consulting with a tax attorney who specializes in gambling taxation. The audit risk is real, and having professional guidance upfront could save significant headaches later. One practical suggestion: Start with impeccable documentation this year but consider filing as a hobby gambler initially. This gives you time to build a stronger case for professional status while maintaining detailed records that could support a future change in classification. The strategy of establishing status now for future flexibility is interesting, but make sure the business substance matches the tax treatment from day one.

My accountant told me the IRS has a "hobby loss rule" specifically for this issue. If your business doesn't show a profit in 3 out of 5 consecutive years, they'll assume it's a hobby not a real business. For things like horse breeding or training they give you more leeway (5 out of 7 years). Besides, committing tax fraud isn't worth it. They can hit you with penalties, interest, and in serious cases even criminal charges. The stress of waiting for that audit letter alone would kill me lol.

Just to add somethin nobody mentioned - the IRS also uses a scoring system called DIF (Discriminant Function) that assigns points to tax returns that have unusual patterns or high amounts of deductions comparred to income. High DIF score = higher chance of audit. So even if you think your writing off a bunch of personal stuff as "business expenses" is a good idea, you might be raising your DIF score without realizing it. IRS computers are looking for patterns, not just random returns.

Has anyone used TurboTax or H&R Block software to file amendments for old Robinhood 1099s? I'm in a similar situation and wondering if the process is straightforward with tax software or if I should go to a professional.

One thing I haven't seen mentioned yet is the statute of limitations for unfiled returns. The IRS generally has 3 years from the date you file your return to audit it, but if you never filed at all, there's no statute of limitations - they can come after you indefinitely for those years. This is actually a good reason to get those amendments filed sooner rather than later. Once you file your amended returns, the 3-year clock starts ticking and you'll have some certainty about when the IRS can no longer pursue those years. Also, keep in mind that you can only carry capital losses forward, not backward. So if you had losses in 2020 but gains in 2021, you can't use the 2020 losses to offset the 2021 gains unless you file the 2020 amendment first. The order matters when you're dealing with multiple years of unfiled returns with mixed gains and losses.

First timer with serve card here too! Transcripts updated last night with 846 code for 2/28! The wait is almost over yall 🎉

I'm in the same situation with JH and Serve card! Filed Jan 30th and accepted same day. Been obsessively checking transcripts but still no 846 code. Seeing Oliver got his 846 for 2/28 gives me hope though! The anxiety is real when you see people with other banks already getting their deposits. Thanks for posting this - nice to know we're all in the same boat waiting for PATH to lift 🤞

Don't forget about the tax treaty between the US and New Zealand! It can prevent double taxation on certain types of income. For example, if you're paying NZ taxes on income earned there, you might be able to claim those as a credit against your US tax liability.

As someone who went through this exact situation when I moved from the US to New Zealand in 2019, I feel your pain! The dual residency tax situation is genuinely confusing at first, but it gets easier once you understand the basics. A few additional tips that haven't been mentioned yet: 1. Keep detailed records of your move date and all income sources. The IRS will want to see exactly when you earned what income and where. 2. Don't forget about your US retirement accounts (401k, IRA, etc.) - these need to be reported on your FBAR if the total value exceeds $10,000 at any point during the year, even though you're not contributing to them anymore. 3. If you're planning to stay in NZ long-term, consider whether you want to keep your US bank accounts open. Having them makes some things easier (like direct deposit of any remaining US income), but it also creates ongoing FBAR reporting requirements. 4. New Zealand's tax system is actually pretty straightforward compared to the US, so don't stress too much about the NZ side. Their IRD website has good resources for new residents. The key thing is getting this first year right, which sets the precedent for future filings. Once you have a system in place, it becomes much more routine. Good luck!