I went through this exact same situation two years ago with similar income levels. We ended up doing the religious ceremony without the legal marriage and have successfully filed as single for two tax seasons now. A few practical tips from our experience: 1. Keep excellent documentation of your decision - we have a written record of why we chose not to get a marriage license, which our tax attorney said was smart in case of questions later. 2. Be very careful about beneficiary designations on retirement accounts. We learned that some 401(k) plans require spousal consent for non-spouse beneficiaries, but since we're not legally married, this doesn't apply. However, we had to be explicit with HR that we're unmarried to avoid confusion. 3. Consider the timing if you ever do decide to legally marry later. Getting married on January 1st vs December 31st can make a huge difference in your tax liability for that year. 4. We found that having separate tax preparers actually helped - it avoids any appearance that we're coordinating our returns inappropriately, even though we're doing nothing wrong. The religious ceremony was beautiful and meaningful to us, and we've saved over $15,000 in taxes over two years. For our situation, it was absolutely the right choice.

This is such a fascinating discussion that really highlights the complexities of our tax system. I'm in a similar situation with my partner - we're both high earners and the marriage penalty would cost us significantly. One aspect I haven't seen mentioned yet is how this might affect state taxes too. Some states have different rules or penalties that could either amplify or offset the federal marriage penalty. For example, some states don't have income tax at all, while others have their own marriage penalties or bonuses. Also, has anyone considered the psychological/social aspects of this decision? I worry about constantly having to explain to family, friends, and colleagues why we had a ceremony but aren't "really" married. It seems like it could create awkward situations, especially in professional settings where marital status sometimes comes up (like for benefits enrollment or company events). I'm really torn because the financial logic is clear, but I wonder if the social complexity and potential long-term legal complications outweigh the tax savings. Reading everyone's experiences here is incredibly valuable though - it's not a decision you can make lightly with these income levels where every choice has significant financial implications.

Just a heads-up for anyone applying for a trust EIN - make sure you're clear about what type of trust you have before starting the application. I messed up and had to call to get it fixed. Estate trusts, living trusts, and testamentary trusts are all handled differently. Double check your paperwork first!!

Thanks everyone for all the helpful responses! I ended up going with the online application route after reading through all your advice. @Sophia Gabriel your direct link was exactly what I needed - I had been getting lost in the general IRS website maze. I made sure to gather all my trust documents beforehand and set aside a solid 30 minutes without interruptions. The 15-minute timeout is real, so definitely don't start unless you're ready to finish! For anyone else doing this, the key info you'll need ready is: trust name, date the trust was established, trustee's full name and SSN, and the trust's address. Got my EIN instantly once I submitted the application. The whole process took about 10 minutes once I actually found the right page. Really appreciate everyone sharing their experiences - it made this so much less stressful!

This is such a challenging situation, and I really appreciate everyone sharing their experiences and expertise here. As someone who's been following this discussion, I wanted to add a perspective that might be helpful. The most striking thing about your brother's case is that he actually kept all the physical cash for 35 years - that's almost unprecedented discipline in maintaining records, even if they weren't properly reported. This could actually work in his favor during any disclosure process because it shows he wasn't spending unreported income on lifestyle inflation or hiding assets in complex ways. What concerns me most is the time pressure element that several people have mentioned. Every day he delays increases the risk that some other event (like a banking relationship review, a routine audit, or even a burglary report if someone discovers he has that much cash at home) could trigger IRS attention before he can get ahead of it with voluntary disclosure. From reading all these responses, it seems like the consensus is clear: get a criminal tax defense attorney immediately, understand all available voluntary disclosure options, and create a comprehensive plan before making any deposits or IRS contact. The upfront cost of proper legal representation will likely be a fraction of what poor handling could cost him in penalties, interest, and potential criminal exposure. Has your brother started looking into attorneys yet? Given the complexity and stakes involved, I'd suggest consultations with multiple specialists to make sure he finds someone with specific experience in large voluntary disclosures like this.

This thread has been incredibly informative, and I wanted to share some thoughts as someone who works in banking and has seen similar situations from the financial institution side. When your brother eventually makes this deposit, the bank will absolutely file both a Currency Transaction Report (CTR) and likely a Suspicious Activity Report (SAR). What many people don't realize is that banks have sophisticated software that tracks customer behavior patterns, so even if he had been making smaller deposits over time, the sudden change from zero banking activity to regular cash deposits would have triggered alerts anyway. From the bank's perspective, we're required to ask about the source of large cash deposits. Having a clear, honest explanation prepared (ideally with supporting documentation from his attorney) will make this process much smoother than being evasive or unprepared. One practical consideration that hasn't been mentioned: he should probably open the account at a bank where he doesn't currently have a relationship. This keeps his existing banking separate from what will inevitably become a heavily documented transaction. Also, some banks are more experienced with handling large cash transactions than others - community banks that work with cash-heavy businesses might be more comfortable with the process. The most important thing is that by the time he walks into any bank, he should already have legal representation and a clear disclosure strategy in place. The banking transaction should be the final step in the process, not the first one.

This is all really helpful information! I'm dealing with a similar situation but have one additional question about quarterly estimated taxes. Since I'm treating my eBay selling as a business with Schedule C, do I need to be making quarterly estimated tax payments? My sales have been growing throughout 2024 and I'm worried I might owe a big chunk at tax time. I made about $15K in sales (probably around $8K profit after all expenses), but I haven't been setting aside money for taxes or making quarterly payments. Should I start making estimated payments for 2025, or is there a threshold where this becomes required? I don't want to get hit with penalties, but I also don't want to overpay if it's not necessary for my income level.

One thing I haven't seen mentioned yet is the importance of understanding how eBay's fee structure affects your Schedule C reporting. eBay charges final value fees, payment processing fees, and sometimes listing upgrade fees. All of these are deductible business expenses, but they need to be categorized correctly. The final value fees and payment processing fees would typically go on Line 27a (Other expenses) as "Platform fees" or "Merchant fees." If you use promoted listings or other advertising features, those would go on Line 8 (Advertising). Also, if you're selling in multiple categories on eBay, the fee percentages can vary significantly - electronics might be 12.9% while books could be 15%. This is why it's crucial to download your monthly eBay invoice statements rather than trying to estimate fees. These statements break down exactly what you paid for each type of fee, making your Schedule C much more accurate. I learned this the hard way my first year when I estimated my eBay fees and ended up under-reporting my deductions by almost $400!

Great point about Form 706! I just went through this with my aunt's estate and almost missed that requirement. The estate was just over the threshold at $13.2 million, and none of the consumer tax software I looked at could handle Form 706. One resource that really helped me was the IRS Publication 559 (Survivors, Executors, and Administrators). It's dry reading but explains the difference between estate income and beneficiary distributions pretty clearly. I wish I had read it before starting the 1041 process. Also want to echo the advice about gathering all documents first. I thought I had everything organized but kept finding additional estate expenses weeks later - attorney fees, appraisal costs, even storage fees for estate property. Having to amend a 1041 is not fun and can delay getting the final distributions to beneficiaries. If anyone is dealing with a relatively simple estate (under $100k in income, basic assets), the online software options mentioned here should work fine. But if there's any complexity at all, the peace of mind from using a CPA who specializes in estate returns is worth the extra cost.

I'm currently dealing with my father's estate and this thread has been incredibly helpful! Based on everyone's experiences, I'm leaning toward trying TaxAct Premium first since several people mentioned good results with it. One question I haven't seen addressed - how do these software options handle estimated tax payments for the estate? The estate has been receiving rental income throughout the year, so I'm assuming we'll need to make quarterly payments. Does the software calculate these automatically or do you need to figure that out separately? Also, for those who used professional help, did your CPA handle the entire estate administration or just the tax filing portion? I'm wondering if it makes sense to get professional guidance upfront for the whole process rather than just scrambling at tax time.