Has anyone tried the IRS's W-4 calculator? I think it's free and supposedly helps you figure out proper withholding based on multiple jobs. Wondering if it would solve part of your problem at least for the W2 portion?

I've been dealing with a similar situation - multiple income streams including S-corp income can really mess with your withholding calculations! One tool that's worked well for me is FreeTaxUSA's TaxCaster. It's free and handles S-corp salary vs distribution scenarios better than most consumer tools I've tried. The key thing I learned is that you need to track your S-corp salary as regular W-2 income for withholding purposes, but then account for the self-employment tax savings compared to if that income was straight 1099. Most calculators miss this nuance. Also, don't sleep on making quarterly estimated payments - even if your withholding is close, having that extra buffer from estimated payments can save you from underpayment penalties. I set up automatic transfers to a separate "tax savings" account so the money is there when quarterly dates roll around. The IRS safe harbor rule is your friend too - if you pay 100% of last year's tax liability through withholding + estimated payments (110% if your AGI was over $150k), you won't owe penalties even if you end up owing more at filing time.

The 1099-K threshold changing to $600 for 2024 is going to be a nightmare for casual sellers! I've heard people say they're going to stop selling online altogether because of it. Does anyone know if there's a difference between selling on eBay vs local cash sales through Facebook Marketplace? Like if I sell stuff locally for cash does that somehow avoid all this tax reporting headache?

This is exactly why I keep detailed records of everything I sell online, even though it's a pain. I use a simple Google Sheet with columns for: item description, original purchase price/date, sale price, sale date, and whether it was personal or business. For personal items I can't remember the exact purchase price for, I research what similar items cost when I would have bought them and use that as a reasonable estimate. The key is being consistent and reasonable - the IRS isn't expecting you to remember that you paid $23.47 for a shirt in 2019, but they do want to see that you made a good faith effort to establish your basis. One thing that helped me was going through old credit card and bank statements to find purchases for higher-value items I sold. Most banks let you download several years of transaction history, and searching for store names or amounts can help you piece together purchase records you thought were lost forever.

Great question about supplemental property taxes! I went through this exact same confusion when I bought my home two years ago. Here's what I learned: Yes, supplemental property taxes are generally deductible just like regular property taxes, but there are a few key things to keep in mind: 1. **You can only deduct them if you itemize** - They go on Schedule A along with your other property taxes. 2. **SALT cap applies** - As others mentioned, you're limited to $10,000 total for state and local taxes (including property taxes and state income tax). 3. **Timing matters** - You deduct them in the year you actually paid them, not when they were assessed. 4. **Check your escrow** - Make sure to coordinate with your mortgage company. They might need to adjust your escrow account going forward. For your specific situation about whether to itemize vs. take the standard deduction, you'll want to add up ALL your potential itemized deductions (property taxes, mortgage interest, charitable donations, etc.) and compare that to the standard deduction ($13,850 for single filers, $27,700 for married filing jointly in 2023). The supplemental bill alone might not be enough to make itemizing worthwhile, but combined with your mortgage interest and other deductions, it could push you over the threshold. I'd recommend using tax software or consulting a tax professional to run both scenarios and see which gives you the better result.

Just wanted to add another important consideration that hasn't been mentioned yet - if you're planning to refinance or sell your home within the next few years, keep copies of all your supplemental property tax documentation! I learned this the hard way when refinancing. The lender wanted to see the complete property tax history to properly calculate my new escrow payments, and I had to scramble to get copies of my supplemental bills from two years prior. Having everything organized made the process much smoother the second time around. Also, if you're using a tax preparer, make sure to bring both your regular property tax statement AND the supplemental bill. Some preparers aren't as familiar with supplemental assessments and might miss including it in your deductions. I caught this mistake with my first preparer and it would have cost me about $400 in additional taxes. One last tip - if your supplemental bill seems unusually high compared to what you expected based on your purchase price, you have the right to appeal the assessment in most states. The deadline is usually pretty tight (often 60-90 days), so don't wait if you think there's an error!

Does the 92.35% ever change? Like does Congress adjust this percentage sometimes or has it been the same forever? Just curious if I need to check this number every year.

Great explanation from everyone here! As someone who's been self-employed for about 5 years now, I can confirm that understanding Schedule SE gets much easier once you grasp that 92.35% concept. One thing I'd add for Gabriel - don't forget about the additional Medicare tax if your self-employment income gets higher in future years. Once your combined wages and self-employment income exceed $200,000 (or $250,000 if married filing jointly), there's an additional 0.9% Medicare tax that applies. It doesn't affect the 92.35% calculation, but it's something to be aware of as your freelance business grows. Also, remember that you can deduct half of your self-employment tax as an adjustment to income on your Form 1040. This is separate from the 92.35% calculation but provides additional tax relief. The IRS basically recognizes that as a self-employed person, you're paying both the employee and employer portions of these taxes, so they give you this deduction to help level the playing field. Keep good records of your business expenses like others mentioned - every legitimate deduction reduces both your income tax AND your self-employment tax burden!

Just to add to the confusion lol - if you're a business that doesn't use the calendar year (like my company that uses July-June fiscal year), the tax year can be completely different! Our "2024 tax year" actually ended in June 2024 and we already filed those taxes. Tax years are the worst!

Great question! As someone who works in tax preparation, I always tell clients that during filing season (Jan-Apr), we're technically in the "2024 tax year" since that's what we're filing. But I like to be specific and say something like "We're currently filing 2024 tax returns, but any income you earn in 2025 will be reported on your 2025 return next year." The confusion is totally understandable because "tax year" can mean different things depending on whether you're talking about filing, earning income, or making estimated payments. When in doubt, just ask what they're specifically trying to figure out - are they asking about filing taxes now, or planning for income they're currently earning?