Just wanted to add something important about the timing requirements that hasn't been mentioned yet. When you're dealing with an involuntary conversion like your flood situation, the 2-year replacement period starts from the end of the tax year in which you first realized the gain, not from when the casualty occurred. So if your truck was totaled in 2024 and you received the insurance settlement in 2024, you have until December 31, 2026 to acquire qualified replacement property and still be eligible for the Section 1033 deferral election. This is crucial because if you miss this deadline, you'll be required to recognize the gain in the year it was realized. Also, since you mentioned you already purchased the replacement truck for $47,000, make sure you have clear documentation showing the purchase date falls within this replacement period. The IRS will want to verify this timing if they ever examine your return. Good luck with getting everything sorted out!

Great discussion everyone! As someone who's dealt with several involuntary conversions over the years, I want to emphasize one often-overlooked aspect: make sure to document EVERYTHING related to the casualty event itself. Beyond the insurance paperwork, keep photos of the flood damage, weather reports from that day, any FEMA disaster declarations for your area, and correspondence with your insurance adjuster. The IRS may want to verify that this was truly an involuntary conversion and not a voluntary sale disguised as a casualty. Also, if this flood was part of a federally declared disaster, you might qualify for extended replacement periods (up to 4 years instead of 2) and potentially other tax benefits. Worth checking with FEMA's disaster database to see if your area qualified for any special declarations. This could give you even more flexibility if you need to make additional replacements or adjustments to your business property in the future. The fact that you're getting your documentation together before meeting with your CPA shows you're on the right track. Having all the forms, election statement, and supporting documents ready will make that meeting much more productive!

One thing nobody's mentioned - if you're using the iPhone for product photography, you might want to also deduct photography accessories like a ring light, tripod, maybe even photo editing software if you use it. All of these would be legitimate business expenses too since they directly relate to your Amazon sales activity. I sell on Etsy and deduct all my product photography equipment. Just make sure everything passes the "ordinary and necessary" test for your business. And keep those receipts organized!

Don't forget to consider the timing of your purchase if you're planning to deduct it! If you buy the iPhone late in the tax year, you might want to start using it for business purposes immediately to establish the business use pattern. Also, I'd recommend setting up a separate Apple ID or at least organizing your apps so you can clearly distinguish between business and personal use. Having your photography apps, business communication apps, and Amazon seller app grouped together makes it easier to demonstrate the business purpose if you ever need to justify the deduction. One more tip - if you're taking the business use percentage approach, consider taking screenshots of your photo gallery periodically showing the ratio of business photos to personal ones. It's a simple way to document your usage pattern over time.

Been there. Done that. Got the t-shirt. Called 27 times last month. Finally got through on a Thursday afternoon. Around 2pm Eastern. Wait was only 25 minutes. Much better than mornings. Everyone calls in the morning. Try afternoon instead. Counterintuitive but works. Also helps to have all your docs ready. They'll ask for verification. SSN. Filing status. Address. Previous year AGI. Have it all handy.

I've been dealing with IRS phone struggles for years, and here's what I've learned through trial and error: The key is persistence and timing. I actually keep a spreadsheet tracking my call attempts - sounds crazy but it helps identify patterns. Best success rate I've had is calling on Wednesday mornings between 7:05-7:15am EST (avoid the 7:00 rush). For investment income issues specifically, try pressing 2 for personal income tax, then 4 for "other tax questions" instead of the forms option. This route seems less congested. Also, if you get the "due to high call volume" message, don't hang up immediately - sometimes it will still put you in queue after a 30-second pause. Pro tip: Use a headset or speakerphone and do other work while waiting. I've learned to be productive during those 45+ minute holds. And always call back if you get disconnected - I've noticed they sometimes have system resets around lunch time that clear up the queues temporarily. The investment reporting deadline stress is real, but you've got this! Keep trying different times and menu combinations.

I've been following this thread with great interest as I'm currently dealing with a similar nightmare scenario. The IRS rejected my 2021 1120-S claiming they have no record of my Form 2553, despite having filed it properly and operating as an S-corp for years. What really caught my attention in this discussion is the combination of approaches mentioned - the systematic documentation requests (Business Master File Account Transcript, Form 4506-T) paired with the newer tools like taxr.ai for analysis and Claimyr for actually getting through to the right IRS department. I'm particularly intrigued by Hattie's point about requesting the complete account transcript. In my case, the IRS has been processing my quarterly employment tax returns as an S-corp for three years, but suddenly claims they have no record of the election for my annual return. This system inconsistency seems to be exactly what these transcripts would reveal. For dissolved entities like yours, I'd also suggest checking if your state has any pending tax issues that might be creating federal complications. In some cases, state-level entity problems can cause the IRS to question or override federal elections. The timeline pressure you're under makes this even more critical. Based on what I've read here, I'd probably pursue multiple approaches simultaneously - file for the transcripts and protective claim while using one of the callback services to get through to the Business Entity department directly. The worst thing would be to let deadlines pass while waiting for one approach to work.

I've been dealing with IRS entity classification issues for years as a tax professional, and this thread has some excellent advice. I want to emphasize a few critical points for your situation: First, the fact that your original 1120-S was accepted is huge evidence in your favor. The IRS has internal controls that should have rejected it immediately if there was truly no S-corp election on file. This acceptance creates what we call "administrative estoppel" - they can't now claim they never recognized your status when they previously processed returns based on that status. Second, since your company is dissolved, you're working against some strict deadlines. The IRS generally allows 3 years and 75 days from the original due date to correct entity elections, but dissolution can complicate this. I'd strongly recommend filing Form 9100 (Application for Extension of Time) immediately while you gather your documentation. This preserves your rights to retroactive relief even if the standard deadlines have passed. Third, beyond the excellent suggestions about transcripts and callback services, consider requesting a copy of your complete IRS file using the Freedom of Information Act (FOIA). Sometimes documents exist in the system but aren't showing up in standard searches. A FOIA request forces them to do a comprehensive search. The combination approach mentioned by others is spot-on - use the systematic documentation requests to build your case while using callback services to get to the right people who can actually resolve it. Time is your enemy here, so parallel processing is essential.

Something to consider - if one of you makes significantly more than the other, you might want to adjust your withholding differently. When my wife and I got married, we found that we needed to withhold extra from the higher-earning spouse to avoid owing at tax time. Also, don't forget about that side job with tips! Tips are taxable income and if they're not withholding enough for those, you could end up with a surprise tax bill. I'd recommend putting a little extra withholding on that job's W-4.

One thing nobody's mentioned - you can always adjust your W-4 throughout the year if you find the withholding isn't right! My husband and I got married last year and had to tweak our withholding twice before we got it right. You might consider starting conservative (slightly higher withholding) and then after a few months, use the IRS Withholding Estimator again to see if you're on track. Many people don't realize you can submit a new W-4 to your employer anytime your situation changes.