One thing I learned the hard way - keep really good records of all the expenses related to the property between inheritance and sale! We paid property taxes, insurance, some repairs, and utilities while the house was on the market. These costs can often be deducted from your proceeds when calculating your gain. Our sale was last year, and I'm STILL trying to track down all these expenses because I didn't keep good records. 🤦‍♀️ Don't be like me!

Great question! Yes, HOA fees paid between inheritance and sale are typically deductible as selling expenses. These are considered costs of maintaining the property while it's being marketed for sale. Keep all your HOA payment receipts and any other maintenance costs like utilities, insurance, property taxes, and repairs during the holding period. Just make sure to only deduct your 50% share of these expenses (matching your ownership percentage) when you report everything on Form 8949. Your brother should deduct his 50% share on his return. Also, since this is a condo, don't forget to check if there were any special assessments during that time period - those would also be deductible if you paid them while preparing the property for sale.

Great question about adjusting withholding after buying a home! I went through this exact situation a couple years ago. One thing to keep in mind is that the mortgage interest deduction isn't as straightforward as it used to be since the Tax Cuts and Jobs Act increased the standard deduction significantly. Before making any W-4 changes, I'd recommend calculating whether you'll actually be itemizing or taking the standard deduction. For 2024, you need more than $14,600 in itemized deductions as a single filer (or $29,200 if married filing jointly) to beat the standard deduction. This includes your mortgage interest, property taxes, state income taxes, and any other deductible expenses. If your total itemized deductions don't exceed the standard deduction, then buying the house won't actually change your tax liability much, and you might not need to adjust your withholding at all. If you will be itemizing, then yes, definitely use one of the tools mentioned here like the IRS withholding calculator or consider talking to a tax professional. They can help you figure out the exact adjustment needed based on your specific situation.

This is exactly why I love this community - so much helpful advice! As someone who works in tax preparation, I'd add one more consideration: timing your withholding adjustment strategically throughout the year. Since you bought in March, you'll have 10 months of mortgage interest to deduct this year. But next year you'll have the full 12 months, which means your tax situation will be different between this year and next year. My suggestion would be to calculate your withholding adjustment based on this year's partial mortgage interest first, then plan to readjust your W-4 again in January for the full-year impact. This prevents you from over-adjusting and ending up owing money at tax time. Also, don't forget about property taxes if you're escrowing them - those count toward your itemized deductions too and can make a significant difference in whether itemizing beats the standard deduction. The tools mentioned here (IRS calculator, TurboTax calculator, taxr.ai) are all solid options. Pick whichever interface feels most comfortable to you and run the numbers!

I'm dealing with this exact same situation right now! My S corp is profitable but our personal paychecks are tight, and medical expenses have been killing us. Reading through all these responses has been incredibly enlightening - I had no idea about QSEHRA or the proper way to structure medical reimbursements. The consensus seems clear: don't just charge medical expenses to the business card (even though that would be so much easier!), but instead set up a formal reimbursement arrangement. I'm leaning toward QSEHRA since the $11,800 family limit would cover most of our annual medical costs. One thing I'm curious about that I didn't see addressed - how do you handle medical expenses that occur before you get the QSEHRA formally established? Should I hold off on any reimbursements until the plan document is properly reviewed and in place, or can I pay expenses personally now with the intention of setting up reimbursements once everything is formalized? Also, does anyone know if there are timing requirements for how quickly you need to process reimbursements after submitting expenses? I want to make sure I'm not creating any compliance issues by batching them monthly vs. processing them more frequently. The separate bank account suggestion is brilliant - definitely implementing that. Thanks everyone for sharing your real experiences rather than just pointing to IRS publications!

As a small business owner who went through this exact same struggle, I can't emphasize enough how much properly setting up medical expense reimbursements through your S corp can help with cash flow issues! The advice here about QSEHRA is spot on - it's really the best option for small operations like yours. I set mine up about 18 months ago and it's been a game changer. The $11,800 family limit covers most of our annual medical costs, and the tax savings have given us exactly the breathing room we needed. A few practical tips from my experience: Start simple with your documentation system - don't overcomplicate it. I use a basic spreadsheet and a dedicated folder for receipts, and it takes maybe 20 minutes a month to process everything. The separate bank account suggestion is absolutely worth doing - it makes everything so much cleaner for bookkeeping and gives you confidence you're doing things right. Also, don't let the setup process intimidate you. Yes, there's some initial paperwork, but once you get the system running it becomes routine. I was overwhelmed at first too, but the peace of mind knowing everything is legitimate and properly documented is huge. The key is just getting started - every month you delay is money you're leaving on the table. Your business is already generating good revenue, so you have the perfect opportunity to implement this properly and start seeing immediate benefits in your personal cash flow.

I'm going through the exact same thing! My transcript shows DDD for today with Chime and I've been refreshing my app every few minutes since 6am with absolutely nothing. This is my first time using Chime for my tax refund and I was starting to panic thinking I entered my routing/account number wrong or something. Reading through all these comments is honestly such a huge relief - I had no idea that Chime processes IRS deposits in batches throughout the day rather than all at once in the morning. It's so reassuring to see that @Olivia Kay and @Jibriel Kohn both got theirs later today and that this seems to be completely normal during tax season. I really needed this money for rent that's due Monday, so the anxiety has been real! Going to try my best to stop obsessively checking and wait until this evening. Thank you everyone for sharing your experiences - it really helps to know we're all in this together and that the delay doesn't mean something went wrong!

Same situation here! My transcript shows DDD for today with Chime and I've been checking constantly since this morning - absolutely nothing yet. This is my first year using Chime for my refund and I was getting really worried something went wrong. Reading through all these comments is incredibly reassuring though! It sounds like Chime really does process IRS deposits throughout the day in batches rather than all at once. Super helpful to see that @Olivia Kay and @Jibriel Kohn both got theirs later today - gives me hope that mine will hit by tonight. I had no idea this was normal for tax season. The waiting is brutal when you're counting on that money, but at least now I know it's just how their system works. Going to try to be patient and check back around 6pm instead of refreshing every 10 minutes!

Great question about Wise! I've been using it alongside PayPal for the past 18 months and went through the reporting analysis when my country implemented CRS last year. Wise is generally treated as a financial institution under OECD reporting frameworks, similar to PayPal and Payoneer. In fact, because Wise operates as an electronic money institution (EMI) with banking licenses in multiple jurisdictions, it's often subject to even more comprehensive reporting requirements than traditional payment processors. What I found particularly important with Wise is that they hold your money in actual bank accounts (pooled, but still traditional banking infrastructure), which means they fall squarely under CRS definitions of "financial institutions." This is different from some payment processors that might have more ambiguous classifications. The multi-currency aspect of Wise also adds complexity - if you're holding balances in different currencies, each currency balance might be evaluated separately against reporting thresholds, or they might be combined using exchange rates. This varies by country, but it's something to track carefully. From a practical standpoint, Wise actually makes documentation easier in some ways because their transaction history and balance tracking tools are quite robust. Their monthly statements are detailed and easy to export, which helped a lot when I needed to provide historical data to my tax advisor. I'd definitely include your Wise accounts in any documentation routine you set up. The same principles apply - track monthly peak balances, major inflows, and any transfers between platforms. Better to have comprehensive records across all platforms than to miss something that becomes reportable later.

This has been such an incredibly valuable discussion! As a newcomer to international freelancing, I had no idea about the complexity of OECD reporting requirements until reading through everyone's experiences here. I've been doing small design projects through Fiverr and getting paid via PayPal for about 6 months now, mostly keeping the money in my PayPal account for convenience. Reading about the retrospective reporting requirements and the "highest balance during the year" rule has been a real eye-opener - I never considered that even my modest freelance earnings could potentially trigger international reporting obligations. What really strikes me is how quickly this landscape is changing. It sounds like strategies that freelancers used even recently to stay "under the radar" are becoming obsolete as these platforms get integrated into global financial reporting systems. I'm definitely implementing Sofia's monthly documentation routine starting immediately. The 10-minute monthly screenshot approach seems so manageable, and tracking peak balances, monthly inflows, and platform transfers covers exactly what these reporting frameworks seem to focus on. One question for the group: for someone just starting out with relatively small amounts (my highest monthly balance has been around $3,000), is it worth consulting with a tax professional now, or better to get my documentation organized first and seek professional advice once my income grows or if my country announces CRS implementation? Thanks to everyone for sharing such practical, real-world guidance - this is exactly the kind of insight that's impossible to find in official tax documentation but crucial for understanding what we're actually dealing with as the international freelance economy evolves!