


Ask the community...
I work at a bank (not for the IRS) and I can tell you that sending 183,000 money orders would probably result in them being returned to you unprocessed. We have policies about handling large volumes of instruments like this, and I'm sure the IRS does too. Plus, money orders usually cost $1-2 each to purchase, so you'd be spending an extra $183k-$366k just on fees! If you're serious about resolving your tax issue, consider reaching out to a tax attorney who specializes in IRS disputes. The upfront cost might seem high, but they often save you way more than their fee in the long run.
I never thought about the fees for the money orders! That would be wild to pay double just to make a point. Do tax attorneys actually have any success fighting the IRS? Everyone I've talked to makes them sound like an unstoppable force.
Tax attorneys absolutely can be successful against the IRS. The key is finding one who specializes specifically in tax controversy or tax resolution, not just a general tax preparer. The IRS makes mistakes all the time, and they have various programs like Offers in Compromise that can reduce legitimate tax debts. I've seen clients get tax bills reduced by 50-70% with the right representation. The IRS is powerful but not infallible, and they have internal procedures for resolving disputes. The biggest mistake people make is trying to handle complex tax issues themselves without understanding the technical aspects of tax law.
Have you considered requesting an audit reconsideration? If the amount is incorrect, you can submit documentation showing why the assessment is wrong. I had a $68k bill that was based on incorrect information from my employer, and after filing for reconsideration with the right documentation, it was reduced to under $4k.
This is the real answer! Audit reconsideration saved me when I had a similar issue. The key is having all your documentation extremely organized and being very specific about what errors were made in the original assessment.
Has anyone noticed how dumb it is that they don't let you use your unused AOC years for grad school? Like... why does it matter what level of education it is if you haven't used all 4 years? The tax code makes no sense sometimes!
The AOC was specifically designed to encourage and support undergraduate education. The government allocated funds differently for different education levels. It's not about logic so much as different policy priorities. Graduate education is subsidized through other mechanisms like the Lifetime Learning Credit.
FYI - make sure to keep really good records of which education credits you claim each year. My son had his return flagged for review because we apparently claimed the AOC for too many years (we didn't realize his community college year counted toward the 4-year limit). The IRS is definitely tracking this stuff!
Here's what people aren't mentioning - the type of settlement matters HUGELY for how it's taxed. If your settlement was for physical injuries or illness, that part is generally NOT taxable (even the attorney portion). If it was for emotional distress, lost wages, or punitive damages, different rules apply. What was your settlement for? That makes all the difference in whether you pay taxes on the full amount or not. Some settlements are completely tax-free while others are fully taxable.
It was an employment lawsuit - wrongful termination and some back wages. Does that change things? I'm still confused about whether I need to itemize to deduct the attorney fees or if I can take the standard deduction AND still deduct the attorney portion somehow.
That's actually good news! For employment-related lawsuits including wrongful termination, you can deduct your attorney fees as an "above-the-line" deduction. This means you can still take the standard deduction AND deduct your attorney fees. You'll want to look at Schedule 1, Line 24 "Other adjustments" and write "ATTORNEY FEES" next to it with the amount. This way you're not taxed on money that went straight to your attorney. Employment cases specifically have this special treatment thanks to a tax law change that was made specifically to address this unfair situation.
The issue isn't just with settlements - it's with our stupid tax code in general. You're being double-taxed on money you never received! Your lawyer also pays taxes on that same money as income. So the government gets to tax the same dollar twice. And depending on your income level and state, you might end up paying 40%+ in taxes on money that you never even saw. The whole system is designed to extract maximum revenue.
While I agree the tax code is complex, this isn't quite accurate. For employment-related cases (which OP mentioned in comments), the attorney fees can be deducted as an above-the-line deduction. Congress actually fixed this problem for certain types of cases, including employment claims, civil rights cases, and whistleblower claims specifically to prevent double taxation.
I've worked with several non-profits on similar structures. One approach to consider is forming a separate for-profit entity that acquires the land, with investors who are looking for the tax benefits. The non-profit would then be granted specific rights to implement the regenerative agriculture projects. The key is making sure the conservation easement genuinely restricts development rights that have real value. If you're looking at agricultural land with legitimate development potential that you're permanently restricting, that can work. But if you're trying to inflate values artificially, you're heading for trouble.
Thanks for sharing this structure! I'm curious - how do you typically handle the ongoing relationship between the for-profit entity that holds the land and the non-profit doing the regenerative work? Is there a lease arrangement, or do you set up some kind of management agreement?
We typically use a long-term management agreement that gives the non-profit the right to implement their regenerative programs while the for-profit entity maintains ownership. This agreement needs to be established before the easement is placed, as it becomes part of the baseline documentation. For funding, we usually structure it so a portion of the tax benefit received by investors flows to the non-profit through a contractual arrangement. This provides ongoing operational funding beyond just the initial land access. Be careful though - the management fees must be reasonable and market-based, or the IRS might view the entire arrangement as a disguised donation scheme rather than a legitimate business structure.
Has anyone tried using partnership structures where investors get both tax benefits AND a share of agricultural revenue? We set up something similar for a client where they placed a conservation easement on 70% of the property, but kept 30% available for sustainable agricultural production. The investors got their tax deduction plus ongoing income from the farming operation.
Declan Ramirez
3 Another important thing to consider - if your girlfriend claims the kids with such low income, she might qualify for other government benefits too. When I was in a similar situation, my tax refund helped me qualify for education grants that completely covered my associate's degree. Make sure she also checks if this will affect any benefits she's already receiving. Sometimes a big tax refund can temporarily push you over income limits for certain programs, so plan accordingly!
0 coins
Declan Ramirez
ā¢17 This is really good advice! My sister got a huge refund from EIC and it messed up her Medicaid for two months because it counted as income. She had to pay out of pocket for her prescriptions until it got sorted out. Definitely worth looking into how it affects other benefits.
0 coins
Declan Ramirez
ā¢3 Absolutely right about the potential Medicaid issue. The good news is that tax refunds only count as a resource for 12 months after receiving them for Medicaid purposes, so it's temporary. For SNAP benefits (food stamps), federal tax refunds don't count as income at all. For education grants, the FAFSA doesn't count tax refunds as income either, which is why it can be such a good opportunity for low-income parents. I was able to use my refund to cover childcare while I took classes, and the Pell Grant covered everything else. Changed my whole career trajectory!
0 coins
Declan Ramirez
14 Just to add another perspective - I was in your girlfriend's exact situation in 2022. I only made about $5800 that year while my boyfriend supported us and our twins. I claimed both kids and received almost $11,000 in tax refunds through EIC, Child Tax Credit, and Recovery Rebate Credit (that was during Covid). The only issue we ran into was that my boyfriend had already claimed one of our kids the previous year, so the IRS flagged our returns for review. We had to submit extra paperwork showing our living situation had changed, but ultimately everything was approved. Just document everything - keep records showing the kids live with you both (school records, medical records), proof of your address, etc. Better safe than sorry!
0 coins
Declan Ramirez
ā¢9 Did you have to mail in your return or could you still e-file? I heard the IRS makes you paper file if you're claiming kids with really low income since it triggers some kind of review.
0 coins