Has anyone tried calling Intuit directly? Maybe they can help? This seems like a massive faillure on their end.

I'm dealing with this exact same issue right now! Got my settlement check for $34 last week and it's been rejected at three different places - my credit union, Chase, and even tried at a check cashing place. The check cashing place said something about the routing number not validating properly in their system. It's so frustrating because like you said, it's not a huge amount but it's still money we're owed. I'm starting to wonder if they made the checks hard to cash on purpose. Has anyone had any luck contacting the settlement administrator directly to complain about this?

I'm dealing with a similar situation but with a twist - I use multiple business bank accounts for different types of work. Some platforms pay directly to my business checking, others go through PayPal, and a few use Stripe. The complicating factor is that sometimes I transfer money between accounts for cash flow management. So if Platform X pays $800 to PayPal, and I later transfer that $800 to my business checking, I'm worried about creating even more confusion in the paper trail. Has anyone dealt with inter-account transfers while also managing duplicate 1099 reporting? I'm tracking everything in QuickBooks, but I want to make sure I'm not setting myself up for audit problems by having money move between multiple accounts that might each generate their own statements. Should I be treating the inter-account transfers as a separate documentation issue, or does the principle of showing the complete money trail from platform to final deposit still apply even when there are stops along the way?

This thread has been incredibly helpful! I'm in a similar situation but with cryptocurrency payments thrown into the mix. I do freelance work and about 30% of my clients pay me in crypto, which I then convert to USD through exchanges like Coinbase. The crypto exchanges are also issuing 1099s now, and I'm worried about triple reporting - the original platform (like Upwork), the payment processor (if they use one), AND the crypto exchange all potentially reporting the same income. Has anyone dealt with crypto payments in this context? I'm assuming the same principle applies (report everything, then deduct duplicates), but I want to make sure I'm not missing any crypto-specific complications. The conversion rates and timing differences between when I earn the crypto and when I convert it are adding another layer of complexity to my record-keeping. Should I be tracking the USD value at time of earning, time of conversion, or both? And how do I properly document that a $1000 crypto payment from Client A is the same income that Coinbase reports when I convert it to USD?

Has anyone tried GoDaddy Bookkeeping? It's around $10/month and seems to have good reviews for self-employed folks with simple business models like us.

As someone who's been through the 1099 contractor journey myself (freelance marketing consultant), I'd suggest starting with Wave Accounting since it's free and see how it works for your needs. You can always upgrade later if you find you need more features. The most important thing is developing good habits around expense tracking and keeping business/personal finances separate. I learned this the hard way during my first tax season! Make sure whatever system you choose can easily generate Schedule C reports and tracks mileage automatically or with minimal manual input. For insurance brokers specifically, pay close attention to deductions for professional development, licensing fees, E&O insurance premiums, and client entertainment expenses. These can add up to significant tax savings if tracked properly throughout the year.

Has anyone brought up the possibility of a 1031 exchange? If these are investment properties, couldn't OP have done a like-kind exchange instead of a distribution to avoid the immediate tax hit?

This is a perfect example of why getting multiple professional opinions is so important with complex tax situations. Based on what you've described, your second CPA appears to be on the right track. Section 1239 typically applies to sales or exchanges between related parties, but what you're describing sounds like a liquidating distribution followed by a contribution to your LLC - not a direct sale between the S corp and LLC. The key factors that support this interpretation: 1. The S corp received no consideration from the LLC 2. The properties were formally distributed to you as the sole shareholder 3. You then contributed them to your wholly-owned LLC 4. The documentation shows this as a distribution, not a sale While the S corp would still recognize gain on the distribution of appreciated property (which flows through to you), this would typically be treated as capital gains rather than ordinary income under Section 1239. However, don't overlook the step-up in basis issue that Jade mentioned - this could be huge in your situation. When you inherited the S corp shares, they should have received a step-up in basis to fair market value at your father's death. This increased basis might offset much of the gain from the property distribution, especially since only 8 months passed. I'd strongly recommend having a tax attorney review the transaction structure and documentation to confirm the proper characterization and ensure you're not overpaying.

This is a great question and you're smart to double-check! As others have mentioned, you don't need to attach your 83(b) election to your 2024 tax return since you already filed it properly within the 30-day window. One additional tip: consider keeping digital copies of your 83(b) election documents in multiple places (cloud storage, email to yourself, etc.) along with your physical copies. I've seen too many founders scramble years later when they need to prove their election was made for capital gains calculations. Also, if your startup issues any tax documents like Form 1099-B when you eventually sell shares, make sure they reflect the correct basis from your 83(b) election. Sometimes companies don't track this properly and report incorrect information to the IRS, which can create headaches during tax season. You're clearly on top of things by asking these questions early - that attention to detail will serve you well as your startup grows!

Great thread! I went through this exact situation last year and can confirm what others have said - no need to resubmit your 83(b) election with your current tax return since you already filed it properly. One thing I wish I had done earlier was creating a simple spreadsheet to track my equity details. I recorded the grant date, number of shares, exercise price, fair market value at grant, and references to my 83(b) filing. This made it so much easier when my accountant needed the information this tax season. Also, if you're planning to exercise more options or receive additional equity grants in the future, consider whether 83(b) elections make sense for those too. The analysis can be different depending on your company's valuation trajectory and your personal tax situation. Keep those records safe - you'll definitely need them when you eventually have a liquidity event!