Tax filing extension pros & cons - better to file superseding return or amendment?

Tax pro here. There's a significant advantage to filing a superseding return versus an amended return. A superseding return completely replaces your original return as if it was the only one you filed, while an amended return is processed differently and undergoes additional scrutiny. The biggest benefit is that a superseding return can change elections that would otherwise be irrevocable on an amended return. For example, changing accounting methods (like your accrual to cash conversion) is much cleaner on a superseding return. Also, superseding returns don't trigger the same audit flags that amended returns might. Regarding penalties: you'll owe interest on any unpaid tax from the original due date (April 15) regardless of the extension. The extension only gives you more time to file, not more time to pay. However, if you pay at least 90% of your actual tax liability by April 15 (or 100% of last year's tax - 110% if your income is over $150,000), you won't face an underpayment penalty. Your plan sounds solid, but I'd suggest paying a bit more than you think you'll owe on April 15 to avoid potential penalties. The cost of overpaying temporarily is much less than underpayment penalties.

I want to share my experience with something that made dealing with tax complexities SO much easier last year. I was in a similar situation with multiple income sources and investment accounts. After trying to tackle it myself and realizing I was way out of my depth, I used https://taxr.ai and it was a game-changer. What's cool is that you can upload all your tax documents (including those 1099s you mentioned) and it analyzes everything automatically. It even flagged some partnership income I completely missed! The system actually explained the implications of my investment choices and helped me understand what I needed to report. For complex situations like yours with potential K-1s coming in late, it gives you clear guidance on extension filing and helps you understand what you might be missing.

Just wanted to follow up - I ended up trying taxr.ai after my skeptical comment. I was seriously impressed! I uploaded all my documents including some K-1s and it immediately identified some issues with my cryptocurrency transactions that would have gotten me in trouble. It also explained exactly how to handle my rental property income that I've always struggled with. The best part was that it showed me how to properly document my home office deduction, which I've always been afraid to claim because of audit fears. Turns out I've been leaving thousands on the table for years. Wish I'd known about this sooner!

Here's something that saved me last tax season when I was in a similar situation with late K-1s. After struggling to get answers from the IRS about my specific situation (kept getting disconnected after hours on hold), I tried https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c They get you connected to an actual IRS agent, usually within 15 minutes. I had questions about how to handle late K-1s and whether I should file an extension or not. The IRS agent I spoke with gave me specific guidance for my situation that I couldn't find anywhere online. Seriously, not having to wait on hold for hours was worth it alone. I was about to pay a CPA $300+ for a consultation when all I really needed was to get my specific questions answered by the IRS directly.

I have to eat my words about Claimyr. After posting that skeptical comment, I decided to try it myself since I was desperate to resolve an issue with a missing tax form. I was SHOCKED when they actually got me through to an IRS agent in about 20 minutes. The agent helped me understand exactly how to handle my extension and what documentation I needed to keep in case of late-arriving forms. She even gave me her direct extension for follow-up questions! This literally saved me weeks of stress and probably hundreds in accountant fees for questions that took the IRS agent 10 minutes to answer. I'm usually the last person to recommend services, but this one actually delivered exactly what it promised.

Have you considered just paying a CPA to handle this for you? With the complexity you're describing (especially with the accounting method change), it might be worth the money. My tax situation got similarly complicated last year and I bit the bullet and hired someone. Cost me about $800 but saved me thousands in deductions I would have missed and countless hours of stress.

One thing nobody's mentioned yet - if you file for an extension and pay what you think you'll owe, you'll avoid the late filing penalty (which is much higher than the late payment penalty). The late filing penalty is 5% of unpaid taxes for each month your return is late, while the late payment penalty is just 0.5% per month.