Has anyone mentioned penalties yet? IRS failure-to-file penalties can be substantial, even if no tax was owed. But there's good news - the IRS has a First Time Abatement policy that can waive penalties for one tax year if there was a clean compliance history before that.

I went through something very similar when my mother passed two years ago. She had 6 years of unfiled returns, and I was completely overwhelmed as the executor. Here's what I learned that might help: First, definitely get those IRS transcripts - they're your lifeline. But also check with your state's revenue department if your dad lived in a state with income tax. Some states maintain their own records that can fill in gaps. One thing that saved me time and stress was creating a simple spreadsheet for each tax year with columns for different income sources (W-2, 1099-MISC, 1099-NEC, etc.). As you go through the transcripts, you can categorize everything clearly. This made the actual filing much more manageable. Also, don't forget about potential deductions he might have been eligible for - standard deduction, any medical expenses if he was older, etc. Sometimes even with unfiled years, the person might actually be due refunds rather than owing money. The whole process took me about 3 months start to finish, but most of that was waiting for transcripts and correspondence with the IRS. The actual filing once I had everything organized was much faster than I expected.

You're asking the right questions, but I think you're missing some nuanced benefits. Yes, single-member LLCs have weaker liability protection than multi-member ones, but they're not completely useless. The key is understanding what they DO protect against. An LLC can shield you from business debts and contractual obligations. If your business defaults on a loan or can't pay suppliers, creditors generally can't go after your personal house, car, or savings. Where it gets murky is with personal liability - if YOU personally cause harm (malpractice, negligence, etc.), the LLC won't protect you. The tax "disregarded entity" status is actually a feature, not a bug, for many small businesses. It simplifies your taxes while keeping the door open for future elections. Once you hit around $60K+ in profit, you can elect S-Corp status and potentially save thousands in self-employment taxes. The real scam isn't LLCs themselves - it's the cottage industry of services that charge $500+ to file $50 worth of paperwork. Most states let you file directly online for under $200. The ongoing costs (annual reports, etc.) are usually minimal too. Bottom line: LLCs aren't magic bullets, but they're useful tools when set up properly and used as part of a broader business strategy.

As someone who's been through this exact decision process, I think the real issue is that LLCs are often presented as either "essential" or "worthless" when the truth is much more nuanced. You're absolutely right that the liability protection for single-member LLCs is weaker than many people realize. Courts are more willing to pierce the corporate veil when there's only one owner, especially if you haven't maintained strict formalities. But "weaker" doesn't mean "nonexistent." The key insight I wish someone had told me earlier is that LLCs protect you from different types of risks in different ways. They're much better at protecting against business debts and contractual liabilities than they are at protecting against personal torts or professional malpractice claims. Here's what changed my perspective: I realized I was thinking about it backwards. Instead of asking "Is an LLC worth it?" I started asking "What are my specific risks, and how does each business structure address them?" For my consulting business, the main risks were client payment disputes and potential contract breaches - areas where an LLC actually does provide meaningful protection. The tax situation is actually more flexible than it initially appears. Yes, you start as a disregarded entity, but that keeps your options open. As your business grows, you can elect different tax treatments without having to restructure entirely. My recommendation: Don't form an LLC just because everyone says you should, but don't dismiss it just because the protection isn't perfect. Analyze your specific situation, risks, and long-term plans first.

The same thing happened to me but with Spotify! Tax was like 14.2% and I was so confused. Turns out I had moved counties but my billing address was still using my old address which had higher local taxes. Check your billing address in your Apple account. Even if you updated your Apple ID info, sometimes the billing address for subscriptions updates separately.

I work in tax compliance for a digital services company, and what you're experiencing is actually quite common. The 13.6% rate you're seeing is likely a combination of multiple tax layers that Apple has to collect based on your billing address. Here's what's probably happening: your base state sales tax, plus any county tax, city tax, and potentially a specific digital services tax. Many jurisdictions have added special taxes on streaming and digital subscriptions in recent years - some call them "amusement taxes" or "digital goods taxes." Chicago is notorious for this - they have a 9% amusement tax on top of regular Illinois sales tax. If you're in a high-tax area, 13.6% is unfortunately not unusual for digital subscriptions. The key thing to check is your billing address in your Apple account settings. Make sure it's current and accurate, because Apple calculates tax based on that address, not where you physically are when you use the service.

Just a heads up - you might also need to amend your state tax return if you're in a state that offers tax benefits for 401k contributions. The excess amount wouldn't qualify for state tax benefits either. Also, make sure you coordinate with BOTH former employers. Sometimes when you have two jobs in one year, each employer doesn't know about the other's plan, so neither will automatically flag the excess.

One thing that hasn't been mentioned yet - make sure you understand the timing of when you need to take action. Since you haven't filed your 2023 return yet, you actually have until you file that return to get the excess contribution corrected without it being considered a "late" correction. However, the 6% excise tax on Form 5329 will still apply for 2023 since the excess remained in your account past December 31, 2023. The good news is that once you get the corrective distribution, you won't owe the 6% penalty for 2024 and beyond. Also, when working with your plan administrator, make sure they calculate the earnings (or losses) correctly using the "earnings calculation method" - they should track the performance of your specific contributions. If your account lost money during that period, the corrective distribution will actually be less than the $800 you over-contributed. Document everything carefully - keep all correspondence with your plan administrator and make sure you get the proper 1099-R when the distribution is processed. You'll need this for your tax filings.

Just wanted to share a practical tip that's worked for our family. We established a clear written policy for our kids' custodial accounts that we follow rigorously. We only withdraw for: - Educational enrichment beyond basic schooling - Specialized equipment for talents/interests (sports, music, etc.) - Medical expenses not covered by insurance - College visits and preparation - Special savings for major future expenses (car, first apartment deposit) We document everything and keep all receipts. This approach has kept us safe for years, and we've never had issues with audits or questions. Our accountant reviewed our policy and said it was a solid interpretation of the "benefit of child" standard.

Great question about enforcement! While there isn't active day-to-day monitoring of custodial account withdrawals, the enforcement becomes real in a few specific situations: 1. **Child challenges as adult**: Once your child reaches the age of majority, they can legally challenge how you managed their account. If they believe funds were misused, they can take legal action against you as the former custodian. 2. **IRS audits**: If you're audited, the IRS may scrutinize large or frequent withdrawals from custodial accounts, especially if they suspect the funds were used for your benefit rather than the child's. 3. **Divorce proceedings**: Custodial account management often gets scrutinized during divorce cases, particularly if one parent alleges the other misused the child's funds. 4. **Financial aid reviews**: Colleges reviewing financial aid applications may question large withdrawals that don't clearly benefit the student's education. The rules aren't just theoretical - there have been court cases where adult children successfully sued parents for improper use of custodial funds. The key is that while day-to-day enforcement is minimal, the legal framework is there and can be enforced when circumstances warrant it. Better to be overly cautious than face potential legal and financial consequences later.