One important thing nobody's mentioned - if you take 529 distributions for your mortgage, you CANNOT also claim those same housing expenses for other education tax benefits like the Lifetime Learning Credit. That would be double-dipping and is definitely not allowed. Make sure you're maximizing your overall tax benefit by figuring out which approach saves you more in your specific situation!

Great point about not double-dipping with other education tax benefits! This is something I actually learned the hard way when my tax preparer caught it during review. I'd been planning to use 529 funds for my mortgage AND claim the Lifetime Learning Credit for my tuition, but you have to choose one path or the other for any overlapping expenses. In my case, the 529 withdrawal ended up being more beneficial since I could cover a larger portion of my housing costs tax-free, rather than getting a smaller credit. For anyone in this situation, I'd recommend running the numbers both ways before deciding. Sometimes the education credits might actually save you more money than the tax-free 529 withdrawal, especially if you're in a lower tax bracket. It really depends on your specific income level and how much you're planning to withdraw from the 529. Also worth noting - you can still use 529 funds for some expenses (like housing) and claim education credits for others (like tuition and fees), as long as you're not double-counting any single expense. Just keep very clear records of which expenses you're applying to which tax benefit!

Quick tip - don't forget to separate out the land value! I made this mistake my first year with a rental property and had my depreciation rejected. You can only depreciate the building, not the land. Most tax assessor records break this out. Also, keep in mind that gifted property has different holding period rules for capital gains when you eventually sell. The holding period includes the time your dad owned it too!

This is a really complex situation, but you're asking the right questions! Based on what you've described, it sounds like you have a mixed gift/inheritance scenario which does complicate the basis calculation. One thing I'd suggest is checking if your dad filed Form 709 (gift tax return) when he added you to the deed in 2016. Even if no gift tax was owed (due to the annual exclusion or lifetime exemption), he may have filed one anyway. If he did, that form would show the fair market value of the property at the time of the gift, which would be incredibly helpful for your basis calculation. If you can't find a Form 709, using the 2016 tax assessment as a starting point isn't unreasonable, but as others mentioned, you might want to adjust it upward since assessments are typically below market value. You could research what similar properties in your neighborhood sold for in 2016 to get a sense of whether the assessment was in the right ballpark. Also, don't forget to account for any improvements your dad made to the property after his original purchase - those would increase his basis, which would then carry over to you for the gifted portion. The depreciation calculation can definitely be overwhelming, but taking it step by step and documenting your reasoning will serve you well if you're ever questioned about it later.

dont forget to check ur local city tax rate too. my city is 2.5% but my employer was only withholding 1% and i got hit with like $900 i had to pay. not all employers automatically withhold the right city tax amount! especially if ur employer is based in a different city than where u live.

This happened to me too! I was so confused my first year making decent money. The key thing to understand is that your paycheck withholding is based on estimates, but your actual tax liability depends on your total income for the year. A few things that might be happening: 1. Your employer might not be withholding enough for city taxes (super common issue) 2. If you got a raise or bonus during the year, your withholding rate might not have adjusted properly 3. The withholding tables assume you're earning the same amount all year, but if you started the job mid-year or had income changes, it throws off the calculation The good news is this is totally fixable! Get a copy of your most recent paystub and look at exactly what's being withheld for federal, state, and city taxes. Then compare those percentages to the actual tax rates for your area. You'll probably find the city withholding is way too low. You can fix this by submitting a new W-4 to your employer requesting additional withholding. It's annoying to see less in your paycheck now, but way better than getting hit with a big bill next year!

Just a heads up, with business acquisitions like this, make sure you're looking at asset vs. stock purchase implications too! It can make a huge difference in depreciation/amortization deductions. My accountant told me I could have saved like $150k in taxes if I'd structured my purchase differently.

Great thread! I'm going through a similar acquisition right now and wanted to share what I've learned from my tax attorney. One thing that hasn't been mentioned yet is the imputed interest rules under Section 1274. If your interest rate is below the Applicable Federal Rate (AFR), the IRS will impute a higher rate anyway, which could mess up your tax planning. Also, don't forget to consider the allocation of the purchase price among different assets (goodwill, customer lists, equipment, etc.) since different assets have different depreciation schedules. Section 197 intangibles get amortized over 15 years, but some tangible assets might qualify for bonus depreciation. One more tip - if you're planning to use Section 1202 qualified small business stock exemption down the road when you sell, make sure your purchase structure doesn't disqualify you from that benefit. It's worth having this conversation with a tax professional who specializes in business acquisitions before you finalize the deal structure.

Pro tip: keep track of ALL your royalty statements and match them against what actually gets deposited in your account. Record labels are notorious for applying withholding inconsistently, even after you've submitted a properly completed W-8BEN. I had a situation where despite having my W-8BEN on file claiming the 0% treaty rate for royalties from my Japanese distributor, they still withheld 10% for almost a year before I caught it. Had to file forms to reclaim all that withholding.

This is such great information everyone! As someone who's been dealing with international music contracts for a few years, I want to add one more important point that often gets overlooked. Make sure your record label updates their withholding systems after you submit your W-8BEN. I've seen cases where the accounting department receives the form but doesn't properly update their payment processing system, so they continue withholding at the default 30% rate. I always follow up with an email to both my A&R contact and their accounting department about 2 weeks after submitting the W-8BEN, just to confirm it's been processed correctly. Include your taxpayer identification number and the date you submitted the form in your follow-up. Also, keep in mind that W-8BEN forms expire after 3 years, so set a reminder to renew it before it lapses. If it expires, they'll automatically go back to withholding at the full 30% rate until you submit a new one. @Ellie Lopez - since this is your first international deal, I'd definitely recommend keeping detailed records of everything. Save copies of all forms, emails, and payment statements. It'll make your life much easier if you need to reference anything later or if you work with more international labels in the future!