


Ask the community...
Just to add a practical point about IRC 351 vs 368 - don't forget about liabilities! If you're transferring business liabilities along with the assets, this can affect whether you recognize gain even in a supposedly "tax-free" exchange. Under IRC 351, if the liabilities transferred exceed your basis in the assets, you could recognize gain. For IRC 368 reorganizations, the rules vary by reorganization type, but generally, liabilities assumed by the acquiring corporation don't trigger immediate gain recognition (with some exceptions). Also, if you own 82% of your corporation, consider how much control you want post-transaction. Some IRC 368 reorganizations might allow you to have a continuing equity interest/role in the combined business, while others are better for clean breaks.
What about my personal basis in the stock I'm trading in? I started the company with about $250k initial investment. Does that factor into calculating any gain I'd recognize from the cash portion of the deal?
Your personal basis in the stock absolutely factors into calculating the gain on the cash portion. If you receive $1 million in cash and your basis is $250k, you'd recognize a $750k gain on that portion. The stock portion of the exchange may qualify for deferral under IRC 368 depending on which type of reorganization applies. Keep in mind that your initial $250k investment may not be your current basis. If your corporation had retained earnings that were taxed at the corporate level over the years, or if you've made additional capital contributions, these could have increased your basis. Conversely, if you've taken distributions in excess of the corporation's earnings and profits, that might have decreased your basis.
My accountant told me another important difference - IRC 351 is usually for ongoing businesses where you're contributing property and continuing operations, while IRC 368 reorganizations typically involve a significant change in the business structure, ownership, or operations. Also, don't forget about state tax implications! I almost got killed on state taxes after my federal-tax-free reorganization because my state didn't fully conform to the federal treatment. Make sure you check how your state handles these transactions.
Good point about state taxes. I'm in California and they have some weird rules about this. Anyone know if California fully conforms to IRC 351 and 368?
California generally conforms to federal IRC 351 and 368 provisions, but there are some key differences to watch out for. California doesn't automatically adopt all federal tax law changes, so timing can be an issue if there have been recent federal updates. The bigger issue with California is that they have their own additional requirements for some reorganizations and they're much more aggressive about challenging transactions that look like they're structured primarily for tax avoidance. They also have different rules around installment treatment and depreciation recapture that could affect your state tax liability even in a federally tax-free reorganization. I'd definitely recommend getting California-specific advice because the Franchise Tax Board has been known to take positions that differ from the IRS on these complex transactions. The conformity isn't 100% and the differences can be expensive.
Has anyone else noticed that churches are seeing lower donations because of the standard deduction changes? Our pastor mentioned that giving is down about 15% since the tax law changed, and he thinks it's because fewer people itemize now.
Our synagogue actually started educating members about QCDs (qualified charitable distributions) for members over 70.5 years old. Seniors can donate directly from their IRAs which reduces their taxable income even if they take the standard deduction. Maybe churches need to teach their members about these strategies?
You're absolutely right that the higher standard deduction has changed the donation game significantly! I went through the exact same realization a couple years ago. The policy does seem to discourage smaller charitable giving, which is unfortunate. One thing I discovered is that even if you're not getting tax benefits from donations, keeping some basic records can still be worthwhile. If your financial situation changes (job loss, major medical expenses, etc.), you might find yourself in a position where itemizing makes sense again. Also, some states have different rules than federal - my state still gives charitable deduction benefits even when I take the federal standard deduction. The bunching strategy mentioned earlier really works though. I now alternate years - donate $8,000-10,000 every other year instead of $4,000-5,000 annually. Combined with my mortgage interest and property taxes, I can itemize in those heavy donation years and save real money. It requires a bit more planning but the tax savings make it worth it.
That's a really smart point about keeping basic records even when taking the standard deduction! I hadn't thought about how a job loss or major medical expense could suddenly make itemizing worthwhile again. I'm curious about the state deduction benefits you mentioned - do you mind sharing which state? I'm in California and I think we just follow federal rules, but maybe I should double-check that assumption. It would be nice to get some benefit from my donations even in non-bunching years. Also, when you do your bunching strategy, do you just pick charities you normally support and give them larger amounts, or do you seek out specific organizations? I'm wondering if there are any restrictions on how you time the donations within the tax year.
Has anyone else noticed that FreeTaxUSA sometimes gives different results from other tax software? I entered the same info in both FreeTaxUSA and TurboTax for my LLC and got different amounts. Not sure which one is right.
I've used both as well. The difference is usually in how they guide you through business expenses. TurboTax tends to be more thorough in prompting for deductions but costs way more. Double-check that you entered the same business expenses in both. Also make sure you're consistently either attaching or not attaching your 1099s in both software programs.
I had this exact same confusion last year! The key thing to understand is that FreeTaxUSA's "attach to business" feature is essentially asking whether this income should go on Schedule C (business income) or somewhere else on your return. Since you're doing freelance work through your single-member LLC, those 1099-NECs should definitely be attached to your business and reported on Schedule C - even though they have your SSN instead of your EIN. The IRS treats single-member LLCs as "disregarded entities" by default, so for tax purposes, you and your LLC are the same entity. The big jump in your tax bill when you attach them is because Schedule C income is subject to self-employment tax (15.3% for Social Security and Medicare) in addition to regular income tax. When you don't attach them, the software might be treating it as "other income" that doesn't trigger SE tax - but that would be incorrect for freelance work. Here's what I learned: Yes, you'll pay more in taxes by doing it correctly, BUT you can also deduct all your legitimate business expenses (home office, equipment, software, business meals, etc.) which will significantly reduce that taxable income. Make sure you're claiming every expense you're entitled to - it makes a huge difference!
I went through this exact scenario during the 2020 tax year with the pandemic unemployment. The key factor is determining which tax year the unemployment compensation was received. When I filed my amended return (Form 1040-X), I had to include Schedule 1 (Additional Income and Adjustments to Income) where unemployment is reported on Line 7. The process took approximately 20 weeks for the IRS to process my amended return, and I received an additional tax bill of $1,842 due to the unemployment income plus a small penalty for underpayment.
Just to clarify the timeline for everyone who might be confused - unemployment compensation follows a simple rule: report it in the tax year you actually received the payments, not when you filed your return. So if you got unemployment anytime from January 1, 2023 through December 31, 2023, it belongs on your 2023 tax return (even if you file that return in 2024). If you already filed your 2023 return without including 2023 unemployment benefits, you'll need to file Form 1040-X to amend. But if your unemployment started in 2024, you're all set - just include it on next year's return. The 1099-G form you receive will show exactly which year the benefits were paid, so that's your definitive guide.
Angelina Farar
Just wanna add one thing - make sure to update your W4 with your employer ASAP for 2026! While there's no penalty for filing differently than your withholding status, it's best to have your withholding match your expected filing status to avoid surprises next year. The new W4 form doesn't even have a "filing status" checkbox anymore - instead it asks about multiple jobs and spouse working, so complete it accurately for best results.
0 coins
Alberto Souchard
Great question and lots of helpful answers here! Just to add one more perspective - I work in HR and help employees with W4 questions all the time. What everyone's saying is absolutely correct: your W4 withholding elections and your actual tax filing status are completely independent. The W4 is just an estimate tool to help your employer withhold approximately the right amount of taxes throughout the year. Your actual filing status is determined by your marital status on December 31st of the tax year. Since you were married by the end of 2025, you have the option to file either "married filing jointly" or "married filing separately" - regardless of what any W4 forms say. One tip from the employer side: when you do update your W4 (which I'd recommend doing soon for 2026), the new form is much more comprehensive than the old one. It considers your spouse's income, multiple jobs, deductions, and credits to give you more accurate withholding. Take your time filling it out completely rather than just checking a box!
0 coins