I'm seeing a lot of great advice here about installment sales, but I want to add something important that hasn't been mentioned yet - make sure you understand the depreciation recapture implications for that $62k in assets. Even with installment treatment, any depreciation you've claimed on business assets over the years gets "recaptured" and taxed as ordinary income (not capital gains) up to a maximum of 25%. This recapture has to be reported in the year of sale, regardless of when you receive the payments. So while your goodwill portion ($313k) can be spread over the installment period at favorable capital gains rates, you might still owe some ordinary income tax in 2025 on the depreciation recapture from your assets. The exact amount depends on how much depreciation you've claimed over the years. This doesn't change the fact that your CPA is wrong about owing taxes on the full amount, but it's an important nuance that could affect your 2025 tax planning. Make sure whoever gives you that second opinion addresses the depreciation recapture component specifically.

I've been following this thread as someone who went through a business sale two years ago, and I want to echo what everyone else is saying - your CPA is absolutely wrong about this! The installment sale method is specifically designed for situations like yours. I sold my marketing agency with very similar terms (30% down, remainder over 5 years) and only paid taxes on the payments I actually received each year. One thing I wish I had known earlier: even though you can use installment treatment, you'll want to set aside cash from that first $75k payment for quarterly estimated taxes throughout 2025. The IRS still expects you to pay estimated taxes on the installment income as you receive the monthly payments. Also, since you mentioned this isn't finalized yet, consider asking your attorney about including a clause that protects you if the buyer defaults. With installment sales, if the buyer stops paying, you can face some complex tax situations around bad debt deductions and potential recapture of previously reported gains. Get that second opinion ASAP - this kind of mistake could cost you a massive amount of unnecessary taxes upfront when you should be spreading that burden over 6 years!

Has anyone run into the issue of foreign tax credits with acquired SFCs under Section 965? I'm trying to figure out if my client can claim FTCs for foreign taxes paid by the SFC before they acquired it.

This is a great question that comes up frequently with acquired SFCs. Based on my experience with similar situations, you're on the right track focusing on the acquisition date as your starting point. For Section 965 purposes, you only need to include the accumulated post-1986 deferred foreign income that relates to the period when the entity was an SFC with respect to your client. Since your client acquired the SFC a few years back, you would start with the E&P as of the acquisition date and then calculate forward to the November 2, 2017 and December 31, 2017 measurement dates. The key is documenting your methodology clearly. I'd recommend: 1. Starting with the balance sheet/retained earnings as of acquisition date 2. Adding any E&P accumulated from acquisition through the measurement dates 3. Applying any necessary adjustments per the Section 965 regulations 4. Using the higher of the two measurement date amounts If you're missing some interim year data, focus your reconstruction efforts on getting solid numbers for those two specific measurement dates. The IRS guidance doesn't require you to have perfect monthly tracking - just reasonable support for the measurement date calculations. Make sure to keep detailed workpapers showing your approach in case of future questions!

I'm surprised nobody mentioned Form 2210! If you miss estimated payments but have a reasonable cause, you can sometimes get penalties waived by filing this form with your tax return. Valid reasons can include casualty losses, disasters, or other unusual circumstances. Also, the quarterly payment system is not actually quarters of the calendar year, which trips up a lot of new freelancers. The due dates are: - April 15 (for Jan-Mar income) - June 15 (for Apr-May income) - September 15 (for Jun-Aug income) - January 15 of the next year (for Sep-Dec income

@Brady Clean, based on your income level ($3,200-4,000/month), you'll likely owe more than $1,000 in taxes, so you would normally need to make quarterly payments. However, since you started freelancing in April, you might still be okay if you had enough tax withholding from your W-2 job earlier this year. The key is whether your total withholding from January-March covers at least 100% of what you owed in taxes last year (the "safe harbor" rule others mentioned). If it does, you're protected from penalties even if you don't make estimated payments. If you don't qualify for safe harbor, you technically should have made payments by June 15th and September 15th already. But don't stress too much - the penalties aren't catastrophic. You can still make your remaining payments (due January 15th) and minimize further penalties. My recommendation: Calculate whether you qualify for safe harbor first. If not, make a payment for the January 15th deadline and consider catching up on any missed payments. The IRS is generally reasonable about first-time situations, especially if you make a good faith effort to comply going forward.

I've been dealing with a similar situation and wanted to share what I learned after reading through all these helpful responses. Like many others here, I initially thought I needed to somehow retrieve my actual old IP PINs, but after trying the transcript approach that several people recommended, I realized I was asking the wrong question entirely. I requested account transcripts for the years I needed through the IRS website, and they clearly showed my returns were processed without any identity verification issues. This was actually much better proof than having the old PIN numbers would have been - it demonstrates that whatever PIN I used at the time was correct and accepted by the IRS. The key insight for me was understanding that IP PINs are intentionally designed to be temporary security codes that can't be retrieved later. It's not a limitation or oversight - it's a deliberate security feature. The transcript showing clean processing is the real verification you need in most cases. For anyone else facing this issue, I'd strongly recommend starting with requesting those account transcripts first before spending hours on hold with the IRS phone system. You can get them instantly online if you can verify your identity, and they'll likely give you the proof you actually need without the frustration of trying to recover something that's intentionally not recoverable.

I'm new to this community but have been lurking and reading through this thread because I'm facing the exact same issue. Just wanted to thank everyone who shared their experiences - this has been incredibly helpful! Based on all the advice here, I think I was making the same mistake as the original poster by focusing on trying to retrieve the actual old PIN numbers instead of getting the verification I actually need. The explanation that IP PINs are designed to be temporary security codes that expire makes perfect sense from a security standpoint. I'm going to try requesting the account transcripts online first before attempting to call the IRS. From what everyone's saying, the transcripts showing clean processing without error codes is actually better proof that my returns were filed correctly than having the old PIN numbers would be. For what it's worth, I also found one of my old PINs by checking my TaxAct account history as someone suggested earlier. It was buried in the filing details, but it was there. Might be worth checking if you used the same tax software multiple years. Thanks again to everyone who shared their solutions - this thread probably saved me hours of frustration trying to get something that apparently can't be retrieved anyway!

Just a heads up, if they're controlling when and how you work (scheduled shifts, supervision, etc.), you're almost certainly misclassified. Companies do this ALL THE TIME to save money. I was in the same situation with a call center job last year. After filing the SS-8 form, the IRS determined I was an employee, not a contractor. The company got hit with back taxes and penalties, and I got a nice refund check for the extra self-employment taxes I paid! Don't let them get away with it!!

This is exactly why I always tell people to be very careful about contractor classifications! The key thing to remember is that being classified as 1099-NEC means you're paying both the employer AND employee portions of Social Security and Medicare taxes (15.3% total), whereas W2 employees only pay 7.65% with their employer covering the other half. Based on your description - having supervisors, following their schedule, taking calls during set shifts - you sound like you might be misclassified. True independent contractors typically have more control over how, when, and where they do their work. The good news is that if you are misclassified and can prove it through Form SS-8, you could get back thousands in overpaid self-employment taxes. The IRS looks at factors like behavioral control, financial control, and the type of relationship you have with the company. Your situation has several red flags for employee classification rather than contractor.