I work at a tax office (not an accountant, just admin) and see this issue frequently. The IRS has been particularly bad with SEP IRA deductions lately. Look carefully at your 5498 form from your financial institution - make sure the contribution is properly marked for the correct tax year. We've had several clients where the financial institution reported the contribution correctly but checked the wrong tax year box. When this happens, the IRS computer automatically disallows the deduction because they can't match it to their records.

Just wondering - did you check if the IRS applied the refund to any past tax debts or other federal debts? Sometimes they'll take part of your refund for things like old student loans or past tax bills without very clear notification.

My stepdad was in a similar situation and he just decided to liquidate everything without checking the basis issues first. Ended up owing way more in taxes than expected because there was no step-up and he had to use the original basis from like 40 years ago. Don't make that mistake! Get a proper analysis before you sell anything. Either use one of the services mentioned above or talk to a CPA who specializes in trust taxation. The rules around irrevocable grantor trusts are really specific and depend on how the trust was structured.

Another option to consider if the stocks have declined in value and you're concerned about taxes - you could distribute the stocks to the trust beneficiaries first, then they could sell them individually. Depending on the beneficiaries' tax situations, this might provide better overall tax treatment, especially if any of them are in lower tax brackets. But this would depend entirely on the terms of the trust and whether distributions of stock (rather than cash) are permitted. Worth discussing with your trust attorney if that's an option.

Heads up on the Section 179 deduction - make sure you're aware that if your business use drops below 50% within the "recovery period" (which is 5 years for most equipment), you'll have to "recapture" some of the deduction as income. This happened to me with a tractor I bought a few years ago - had to report additional income when my business use dropped.

I started a small excavation business last year and used TurboTax Home & Business to handle my taxes. It worked fine for me and walked through all the Section 179 stuff pretty clearly. The software was like $120 which seemed worth it given the size of the deduction I was taking.

One thing to consider - the IRS is much more likely to pursue cases with large dollar amounts. You mentioned you only made about $9k over 2 years, so the actual tax difference from your incorrect deductions is probably relatively small. The IRS has limited resources and generally focuses on higher-value cases. That's not to say you shouldn't correct the mistake, but the chances of them coming after you specifically with fraud charges over what's likely a few hundred dollars in tax difference is pretty low. They're looking for the big fish who are hiding tens or hundreds of thousands.

Make sure you're clear about what constitutes fraud vs. a mistake. I work in tax preparation, and fraud requires INTENT. The legal standard for civil fraud includes: 1) Deliberate understatement of income 2) Claiming fictitious or inflated deductions 3) Keeping multiple sets of books 4) Making false entries or alterations 5) Claiming personal expenses as business expenses 6) Hiding assets Your situation sounds like it falls under "negligence" rather than fraud. The penalty for negligence is 20% of the underpayment, while civil fraud penalties are 75%. Huge difference! And negligence penalties can often be abated if you have reasonable cause.

Don't forget you can choose between taking the standard mileage deduction (56 cents per mile in 2021) OR itemizing your actual car expenses (gas, maintenance, depreciation, etc.). For most people who only did rideshare briefly, the standard mileage rate is way easier and usually better. But you need to have kept track of your miles!

Make sure you put aside enough for taxes on that Lyft income! Unlike your W-2 job, there's no withholding on 1099 income. You'll owe income tax plus self-employment tax (15.3%) on your profit. Even after deductions, you might be surprised by how much you owe if you're not prepared.