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Just wanted to share my experience - I was in almost identical situation last year. $198k net revenue, single-member LLC, found out about S corps in October. I filed Form 2553 under Rev. Proc. 2013-30 with my tax return for last year. My strategy was setting up payroll for Nov and Dec only, took reasonable salary for those months ($15k total), and documented why this was appropriate given the timing of my election. My S election was accepted without issues. Saved about $4k in taxes even with just 2 months of S-corp status, and now I'm fully set up for this year too. The key was solid documentation explaining the timing of my reasonable compensation decisions.
Wouldn't the IRS question why you only started payroll for 2 months though? I'm worried they'd see that as trying to avoid paying yourself properly for the whole year.
I went through this exact situation two years ago and decided to wait until the following tax year - best decision I made! Here's why: The administrative nightmare of retroactive S-corp compliance isn't just about filing Form 2553. You'd need to: - Set up payroll software and processes - Calculate and pay employment taxes for the entire year - File quarterly 941 forms (which were due months ago) - Potentially face penalties for late payroll tax deposits - Amend your quarterly estimated tax payments With $230k in net revenue, you're probably looking at around $6-8k in SE tax savings, but the compliance costs, penalties, and rushed setup could easily eat half of that. I used the extra time to properly research payroll providers, set up business banking for payroll, and plan my reasonable compensation strategy. When I elected S-corp status for the following year, everything was clean and proper from day one. The peace of mind was worth more than the one-year delay in tax savings. Plus, having a full year of S-corp planning let me optimize other aspects of my business structure that I would have missed if I'd rushed into it.
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 noticed that the information is sometimes slightly different between copies? I swear my state copy had a different withholding amount than my federal copy last year.
This is such a common confusion! I went through the exact same thing my first few years doing taxes. What helped me understand it was thinking of it like carbon copies from the old days - they're all identical information, just labeled for different destinations. Copy B goes with your federal return (if filing paper), Copy 2 goes with state returns (if filing paper), and Copy C is yours to keep. Since you're using tax software, you can literally use any copy to enter the data - I usually just grab whichever one is on top. The software handles all the electronic filing, so those specific copy designations don't matter for e-filing. Just make sure you hang onto at least one copy (Copy C is perfect for this) for your records. Don't feel dumb about not realizing this - the tax system could definitely be clearer about these things!
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.
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.
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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!
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