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I filed the 1023-EZ for my community arts nonprofit 2 years ago and kinda regret it now. We're trying to get some bigger grants and one foundation specifically asked why we used the EZ form and wanted to see all the documentation that would've been in the full 1023. Feels like they dont trust us as much, tbh.
Something else to consider - if you're planning to grow beyond $50k annual revenue in the next few years, it might actually be better to just bite the bullet and do the full 1023 now. I did the EZ form for my youth mentorship program, but then we grew faster than expected and started getting questions from some donors about our status. Technically there's nothing wrong with starting with the EZ form when you qualify, but some larger funders seem to view the full 1023 process as more "serious." Just my experience in the education nonprofit world, might be different in urban agriculture.
You might also want to check your state's tax laws. Some states have lower reporting thresholds than the federal government. In my state, the threshold is only $600 for reporting marketplace sales, even though the federal threshold is much higher.
I hadn't even thought about state taxes! Do you know if states typically use the same forms (Schedule D and 8949) for reporting this kind of income?
Most states use forms that correspond to the federal forms, but they may have different names. Usually your state tax return will ask for information from your federal return, including your Schedule D amounts, and then make adjustments based on state-specific rules. For example, in my state (California), we use Schedule D for capital gains just like the federal return, but some states have their own forms with different names. The good news is that most tax software will automatically handle this for you once you input the information on the federal forms.
I'm curious - did you sell the tickets at significantly higher prices than what you paid? Might be worth checking if your city or state has any anti-scalping laws. Some places have restrictions on how much above face value you can sell tickets for.
Anti-scalping laws vary widely by location and are rarely enforced for individual resellers. Most target large-scale operations. The tax obligation remains regardless of any potential scalping issues.
Just wanted to share what my financial advisor told me about this situation - there's a specific IRS ruling (I think it was 2005-36) that deals with successor beneficiaries of inherited IRAs. If the original beneficiary was already taking RMDs based on the stretch provision (pre-2020), then any successor beneficiary continues that same schedule. The key thing to remember is that nothing "resets" - not the schedule, not the starting date, nothing. Your aunt basically just picks up where your uncle left off.
Does this apply only to the second beneficiary or would it continue if there was a third beneficiary down the line? Like if the aunt also passes away and leaves it to her child?
The same principle applies to any subsequent beneficiaries down the line. If your aunt passes away and names a third beneficiary, that person would continue with the same distribution schedule that was established when your uncle first inherited the IRA. This creates what's sometimes called a "cascading beneficiary" situation, where each new beneficiary must follow the original schedule. No one gets to reset the clock or use their own life expectancy. This is why proper planning for these pre-2020 inherited IRAs is so important - the distribution schedule follows the assets regardless of how many times they change hands.
Make sure you get the original beneficiary paperwork from when your uncle first inherited the IRA! I went through something similar and the IRA custodian tried to tell me I had to take all the money within 5 years, which was totally wrong. But I couldn't prove the correct distribution schedule until I found the original paperwork showing when distributions started.
As someone who worked in estate planning for 15 years, I'll add that Form 4810 is generally considered a best practice, especially when the estate has been fully distributed. The form isn't "asking for an audit" as you feared - it's actually asking for the IRS to assess any tax due promptly so the executor/personal representative can be discharged from liability sooner. Think of it this way - without filing the form, the executor technically remains potentially liable for estate tax issues for the full 3 years. Filing Form 4810 cuts that down to 18 months.
Thanks for the professional perspective! So if the form is filed and the IRS doesn't respond within the 18 months, does that mean they can't come after anyone later if they find an issue? And does filing this form increase the chances of getting audited compared to not filing it?
If the IRS doesn't assess any additional tax within the 18-month period, they generally can't come after the estate or the personal representative after that time has elapsed. There are exceptions for fraud or significant understatements of income, but for a straightforward estate like you described, those wouldn't apply. Filing Form 4810 doesn't increase audit risk in my experience. The IRS doesn't view it as a red flag - it's a standard administrative request. They process thousands of these forms, and they don't trigger special scrutiny. Many tax professionals consider it good practice to file this form precisely because it limits liability exposure.
Has anyone dealt with filing this in Massachusetts specifically? My father's estate is in probate there, and I'm confused about whether the 18-month federal timeframe conflicts with MA requirements.
Massachusetts resident here. When we settled my grandmother's estate last year, our attorney filed the Form 4810 for federal purposes while acknowledging that MA still maintains their own 3-year period for state tax purposes. The two timeframes operate independently - shortening the federal period doesn't affect the state period at all.
Dylan Baskin
Just a heads up - if you're responding to a CP2000 for missing crypto, you might not need to file a full 1040-X amended return. Sometimes you can just send in the corrected Schedule D and Form 8949 along with the CP2000 response form. When I had this situation last year, I called the IRS (which was a nightmare until I finally got through) and they told me I could just complete the response form, check the "I agree with some changes" box, attach the proper Schedule D and 8949 with the missing transactions, and mail it back. Saved me from having to do a full amendment.
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Marcus Williams
ā¢Really? That would be so much easier! How did you calculate the difference in what you owed? Did you still use tax software to figure out the corrected amount or just calculate it manually?
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Dylan Baskin
ā¢I used TurboTax to calculate the correct amounts but didn't actually file an amended return through them. I basically entered all my original tax info plus the missing crypto transactions, saw what the new tax liability was, then compared it to my original return to get the difference. On the CP2000 response form, I entered my recalculated amount which was actually less than what the IRS estimated (they always seem to assume worst-case scenario on crypto gains). I included a brief explanation letter along with my completed Schedule D and 8949 showing all the transactions with correct basis amounts.
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Lauren Wood
Whatever you do, respond to that CP2000 notice ASAP even if you need more time! I ignored mine thinking I had time to figure it out and ended up with additional penalties. If you need more time, you can call and request an extension, but don't just let the deadline pass. Also, keep copies of EVERYTHING and send your response via certified mail so you have proof of when you sent it.
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Ellie Lopez
ā¢This is super important advice. The IRS is really backed up right now, but they don't extend the same courtesy to taxpayers. I learned this the hard way last year.
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