How can you tell which distributions are qualified vs non-qualified? My 1099-DIV has all these different boxes and I'm never sure what they mean.

On your 1099-DIV, qualified dividends will be in Box 1b, while Box 1a shows total ordinary dividends (which includes both qualified and non-qualified). The difference between Box 1a and 1b would be your non-qualified dividends. Capital gain distributions will be in Box 2a. These are the fund's long-term capital gains that get the preferential tax rate. If the fund had to distribute short-term capital gains, those would actually be included in Box 1a as ordinary dividends, not in the capital gains box, which is why it can get confusing!

I've used TurboTax for years with my mutual funds. It works OK if your brokerage provides good 1099s with detailed cost basis info. You can import directly from most major brokerages which helps avoid mistakes. But for older funds where you've been reinvesting for 10+ years, sometimes you need to manually adjust things, which can get complicated in TurboTax.

Does this change if it's a sole proprietorship though? Since the business income passes through to the business owner's personal return anyway? I'm confused about how this works since technically the money would be taxed on someone's personal return either way.

Great question about sole proprietorships. You're right that the income ultimately flows to someone's personal return, but it matters WHO reports it. The income should flow through the Schedule C of the actual business owner (father-in-law), not OP. Even though it's all "personal income" eventually, the proper reporting chain matters. If reported incorrectly as OP's income, they're being taxed on money they never received or controlled. Plus, the father-in-law's business isn't showing its true income, which creates problems for both parties. The key is getting the income attributed to the correct taxpayer, even if both are individuals in the eyes of the IRS.

The Taxpayer Advocate Service can be amazing but they're extremely backlogged right now. I applied for help in January and didn't hear back until April. They're prioritizing cases with immediate hardship (like impending house foreclosure or can't afford medications). Based on what OP described, they might qualify if the tax bill is causing severe financial hardship, but I'd pursue multiple paths simultaneously rather than waiting on TAS.

Did you have to pay any penalties for making the estimated payment after the deadline? I'm in the same boat and worried about that.

I haven't received any penalty notices yet. My accountant explained that the penalties for estimated tax payments are calculated annually when you file your next return, not immediately. Since I have documentation showing I requested the proper application on my original return, we plan to request penalty abatement if any penalties show up on next year's return. The penalty would be pretty small anyway - it's calculated based on the underpayment amount, the period it was underpaid, and a relatively low interest rate. For my amount, we calculated it would be less than $30 even if they did charge it.

That's a pretty cynical take. Having worked in tax preparation for years, I'm confident this is just a processing error. The IRS systems are outdated and understaffed. Never attribute to malice what can be adequately explained by bureaucratic inefficiency.

You're probably right. Just feeling frustrated with the whole tax system right now. I've had so many issues this year with errors and delays. It just feels like the deck is stacked against regular taxpayers sometimes.

I've heard conflicting advice about this. Wouldn't having multiple LLCs mean multiple annual fees, multiple tax filings, etc? Is it really worth the hassle just to separate different types of business activities?

It does mean additional annual fees and separate tax filings, but those costs need to be weighed against your risk exposure. For lending activities specifically, the risks can be significant. If a loan goes bad and there's litigation, having that activity in a separate LLC helps shield your other assets and business ventures. The administrative overhead is something to consider, but most accounting software makes it fairly manageable to maintain separate books. Many states have reasonable annual LLC fees (though some like California are expensive). I've found the peace of mind worth the extra few hundred dollars annually. It's especially important if one activity is high-risk (like lending) while the other is relatively safe.

Texas is indeed pretty business-friendly. I changed my LLC from retail to consulting last year. You don't need to file any amendment with the Secretary of State unless you're changing the actual name of your LLC. The business purpose statement on Texas LLC forms is usually broad enough to cover almost any legal business activity.

Thanks for the info! That's a relief to hear. Did you have to update anything with the Comptroller's office for franchise tax purposes? I'm wondering if changing activities might affect how I file those reports.

Thank you for this advice - you're right that I should respond directly to this notice rather than assuming they'll eventually process the amendment. Did you have to get tax transcripts to resolve your situation? Someone else mentioned those and I'm not sure if I need them.

Yes, tax transcripts were really helpful in my case. They show exactly what the IRS has in their system versus what you filed. You can request them online through the IRS website or have your accountant get them. The transcript will show if your amended return is in their system and whether your $4k payment was properly applied. The other thing to consider is requesting a formal appeal or audit reconsideration. This creates a separate track for resolving your case rather than just waiting for the amendment to be processed, which can take forever. Your accountant should be familiar with this process. The key is to be proactive rather than reactive - don't just wait for the IRS to figure it out.

This is excellent advice. I'm a tax preparer and see this issue multiple times every tax season. The IRS computers just match document numbers, so if the cost basis isn't properly reported, they'll tax the entire proceeds as gain.