Has anyone dealt with FIRPTA withholding for LLCs with foreign partners that own US real estate? We have the regular income withholding figured out, but now we're selling a property and I'm not sure how that interacts with all this.

I've been through this exact confusion with our LLC that has partners in the UK and Australia. The key insight that finally clicked for me is that these are different taxes on different things at different times. Section 1446 withholding (Form 8813) is on the foreign partner's SHARE of partnership income - you withhold this regardless of whether you actually distribute anything. Think of it as withholding on their "allocated" income. Section 1472 (FATCA) withholding is on actual PAYMENTS to foreign entities that haven't provided proper documentation. But here's the crucial part - if you're distributing profits that have already been subject to Section 1446 withholding, and your foreign partner has provided proper W-8 forms, you typically don't need to withhold again under FATCA. The double taxation concern you mentioned is valid - the IRS doesn't want to tax the same income twice. The confusion often comes from not distinguishing between "income allocation" (what triggers 1446) versus "actual distributions" (what might trigger 1472). For your Canadian and UK partners, make sure they provide W-8BEN or W-8BEN-E forms claiming treaty benefits. This documentation helps establish that distributions of previously taxed partnership income shouldn't be subject to additional withholding. I'd recommend documenting which distributions relate to income that's already been subject to 1446 withholding - this creates a clear paper trail showing you're not double-taxing.

Has anyone used TurboTax for handling home office additions? I'm worried it won't handle the complex depreciation schedules correctly. Does the business version cover this stuff or should I pay for a CPA this year?

One thing to consider that hasn't been mentioned yet - if you're planning to use the space 100% for business as you stated, make sure you understand the "exclusive use" test. The IRS is pretty strict about this - it means ONLY business use, no personal activities whatsoever in that space. I learned this the hard way when my accountant told me that even having my kids do homework in my home office occasionally could disqualify the entire deduction. You might want to think about the layout and access to ensure you can truly maintain exclusive business use. Also, since you mentioned this is to avoid buying a bigger house - document that business necessity thoroughly. Keep records showing how your current business operations are constrained by lack of space, client meeting needs, etc. This helps establish the business purpose if the IRS ever questions the addition. The $135k investment sounds substantial, but if properly structured, the tax benefits over time plus avoiding a house purchase could make it very worthwhile. Just make sure you get professional guidance before breaking ground to avoid any costly mistakes in how you set things up.

With your income at $580k, you're definitely going to be phased out of the Child Tax Credit completely. The phaseout for single filers starts at $200,000 and you'd lose the entire credit well before your income level. Your wife at $35k would get the full $2,000 credit, so she should absolutely be the one claiming your child. Also worth noting - if your wife qualifies for Head of Household status (which she might if she's paying more than half the household costs for her and the child), that filing status comes with better tax brackets and a higher standard deduction than single. This could save her even more money beyond just the Child Tax Credit. Don't forget about the Child and Dependent Care Credit for your daycare expenses too! Same logic applies - it's also income-limited, so having your wife claim those expenses will likely result in a bigger benefit than if you tried to claim them.

This is a really smart question to ask! Given your income levels, you're absolutely right that your wife should claim the child. With your $580k income, you're completely phased out of the Child Tax Credit (the phaseout starts at $200k for single filers), while your wife at $35k would get the full $2,000 credit. One additional consideration - since you mention you cover more household expenses, make sure you're both clear on who can legitimately claim Head of Household status. The person claiming the child as a dependent must also be paying more than half the costs of maintaining the home to qualify for HOH. If you're covering most expenses but your wife is claiming the child, she might not meet the HOH requirements and would need to file as single. You might want to consider documenting who pays for what household expenses, or potentially restructuring how you split costs if it makes sense tax-wise. Sometimes shifting some bill payments to the lower-income partner can help them qualify for HOH status, which provides better tax rates and a higher standard deduction on top of the Child Tax Credit savings. Also definitely look into the Child and Dependent Care Credit for your daycare costs - same income limitation logic applies there too!

Has anyone had success fighting a CP2000 for HSA distributions online through the IRS response portal rather than mailing everything? I'm wondering if I should just use their online system or if it's better to send a physical response with all my documentation.

I dealt with this exact same situation last year! You're absolutely right to question it - HSA distributions for qualified medical expenses shouldn't be taxable. The problem is that the IRS computer system sees your 1099-SA showing the distribution but doesn't automatically know it was for qualified expenses. Even though your 1099-SA has Distribution Code 1, you still need to file Form 8889 with your tax return to officially report to the IRS that these were qualified medical expenses. Without Form 8889, their system assumes the entire distribution is taxable income. For your CP2000 response, I'd recommend: 1. Complete Form 8889 for the tax year showing your qualified medical expenses 2. Include copies of your 1099-SA forms 3. Attach receipts or documentation for the medical expenses that match your distribution amounts 4. Write a cover letter explaining that these were qualified medical expenses Keep copies of everything you send! The IRS should accept your explanation once they see the proper documentation. I went through this process and they completely reversed the proposed tax after reviewing my Form 8889 and supporting documents.

Has anyone used a structured settlement instead of taking a lump sum? My tax guy mentioned this might help spread out the tax burden over multiple years.

Great question about EEOC settlements! I went through this exact situation about 18 months ago with a $95K settlement. Here's what I learned that might help: First, make sure your settlement agreement clearly breaks down what each portion represents - back pay, compensatory damages, punitive damages, attorney fees, etc. This is crucial for tax purposes. Back pay gets treated as W-2 wages (subject to employment taxes), while compensatory damages are taxable income but not subject to employment taxes. One key thing - if you had any documented physical symptoms from the workplace stress (ulcers, migraines, high blood pressure, etc.), those portions may qualify as tax-free under IRC Section 104(a)(2). You'll need medical documentation linking these conditions to the workplace discrimination. Also consider timing - if you're close to year-end, you might want to delay the settlement payout until January to push the tax liability into the next year, especially if you expect lower income next year. The "higher tax bracket" fear is common but remember that tax brackets are marginal - only the income above each threshold gets taxed at the higher rate, not your entire income. Still, spreading it out through installments or maximizing deductions can definitely help reduce the overall tax hit. Definitely consult with a tax professional who has experience with employment settlements - regular accountants often miss the nuances of these cases.