Just to add another perspective - I had a similar situation where I was receiving regular Venmo payments from my roommates for shared expenses (rent, utilities, groceries) totaling about $15,000 over the year. I was initially worried about tax implications too. What helped me was keeping a simple spreadsheet tracking what each payment was for, along with the original receipts or bills. This way I had clear documentation that these weren't income-generating activities, just cost-sharing among friends. The Venmo transaction notes are helpful, but having the underlying documentation (like the actual rent bill or utility statement) gives you even stronger proof that these were legitimate reimbursements. The peace of mind is worth the small effort of organizing your records. Plus, if you ever do get questioned, you'll have everything ready to show these were just friends helping each other out financially, not unreported income.

This is such a common worry that I see all the time! You're absolutely right not to stress about this - friend-to-friend reimbursements like what you're describing are definitely not taxable income. The IRS distinguishes between actual income (where you're making money) and reimbursements (where you're just getting back money you already spent). The fact that your transactions are marked as "friends" and have clear notes like "car help" and "paying you back" actually works in your favor. These notes serve as documentation that these aren't business transactions or income-generating activities. Even though the total amount seems large at $10,500, remember that this isn't new money coming to you - it's just your own money being returned after you helped your friend out. You didn't profit from these transactions, so there's no taxable event. Keep those Venmo records with the transaction notes as backup documentation, but you shouldn't need to report any of this as income on your taxes. The new payment app reporting rules are really targeting people who are running businesses through these platforms and not reporting that income, not friends helping each other out financially.

I'm going through this exact same situation right now! Been on hold since around 5:30pm, got transferred about an hour ago, and it's now pushing 9pm. Reading all these experiences has been incredibly reassuring though - I had no idea about the federal policy requiring agents to work through their queue after closing hours. What's really helping me stay motivated is learning that being transferred actually puts you in a specific department's queue rather than general hold, which explains why we're still connected even though they stopped taking new calls at 7pm. I grabbed my tax return and have that line 24 amount ready after reading everyone's tips. It's honestly insane that getting basic tax help requires this kind of marathon endurance, but seeing so many success stories from people who stuck it out until 8:30-9pm gives me hope. At this point I've invested nearly 4 hours - starting fresh tomorrow would probably mean going through this nightmare all over again. Thanks to everyone sharing their experiences - this community support is literally what's keeping me from hanging up right now! For anyone else in the same boat, we're probably closer to the finish line than we think. The evening agents are supposedly more experienced and thorough since they're not dealing with constant new calls. Let's all hang in there! 🙏

I'm actually going through this exact nightmare right now! Been on hold since 4:45pm, got transferred around 6:30pm about my refund delay, and it's now almost 8:45pm. Reading through all these experiences has been such a lifesaver - I honestly had no idea that the IRS has a federal policy requiring agents to work through their entire queue even after the 7pm closing time. As someone completely new to dealing with IRS calls, I was starting to panic thinking I was just listening to hold music while everyone went home for the day. But learning that being transferred actually puts you in a specific department queue rather than the general hold system makes so much sense and explains why I'm still connected. The tips about having your SSN, DOB, and that line 24 amount from your tax return ready have been incredibly helpful - I just grabbed all my documents and have everything written down and ready to go. It's absolutely wild that getting basic tax help requires this kind of marathon endurance test, but seeing all these success stories from people who stuck it out until 8:30-9pm is giving me the motivation to see this through. At this point I've invested over 4 hours into this call - starting fresh tomorrow would probably mean going through this entire nightmare all over again. Thanks to everyone for sharing your experiences and encouragement. For anyone else currently suffering through their own IRS hold marathon, we're probably closer to the finish line than we think! The evening agents are supposedly more experienced since they're not dealing with constant new calls. Let's all hang in there! 💪

I've been dealing with this exact same W4 nightmare for years and finally got it sorted out! Reading through everyone's experiences here really highlights how common this problem is for dual high-income households. Just wanted to add one thing that I haven't seen mentioned much - when you're calculating that additional withholding for Step 4c, make sure you're using the most current year's tax tables. I made the mistake of using old worksheets one year and ended up still owing because the brackets had shifted slightly. Also, for anyone feeling overwhelmed by all the math involved, I found it helpful to think about it this way: if you owed $6,000 last year, that's roughly $230 per paycheck that you were under-withholding (assuming 26 pay periods). So adding that amount to Step 4c gets you much closer to breaking even, then you can fine-tune from there. The peace of mind from not getting hit with a massive tax bill is absolutely worth the reduced take-home pay during the year. Plus, you avoid any potential underpayment penalties if you owe too much. One last tip - if your employer offers it, consider switching to having taxes calculated per paycheck rather than using the annual method. Some payroll systems default to annual calculations which can cause issues with withholding accuracy when you have variable income throughout the year.

I've been through this exact same situation and the advice in this thread is spot on! Just wanted to add a few practical tips from my experience fixing our W4 mess: **Document everything** - Keep a spreadsheet tracking what changes you make and when. I noted the date of each W4 update, what we changed, and our reasons. This helped tremendously when doing mid-year checkups to see if our adjustments were working. **Start conservative** - If the tables suggest adding $575 per paycheck in Step 4c, consider starting with something like $450 and checking your progress after a few months. It's easier to increase withholding than to deal with a massive refund if you over-correct. **Coordinate with your spouse** - Make sure you're both clear on who's claiming what. We actually put a note in our phones about which spouse claims the kids and how we split the extra withholding so we don't forget when updating W4s in future years. **Check your first few paystubs** - After submitting new W4s, verify that the changes actually took effect correctly. I caught a payroll processing error that would have cost us thousands by checking my stub right away. The reduced take-home pay definitely feels painful at first, but owing $8K+ in April is so much worse. You're making the right move by fixing this early in the year - you'll have the full year for proper withholding to take effect!

One thing nobody mentioned yet - make sure you're paying quarterly estimated taxes on your tutoring income! I got hit with an underpayment penalty my first year as a contractor because I didn't realize I needed to make payments throughout the year.

As someone who's been doing freelance consulting work for a few years, I can confirm that the QBI deduction is a real game-changer for independent contractors like yourself! Your tutoring income absolutely qualifies. One thing I'd add to the excellent advice already given - since you're working 30 hours a week, this is clearly a substantial business activity, not just a hobby. That strengthens your position for claiming business deductions. Also, don't stress too much about the complexity. The IRS has Publication 535 (Business Expenses) and Publication 587 (Business Use of Your Home) that explain everything in detail, but honestly, most tax software will walk you through the QBI calculation once you enter your Schedule C information. The key point everyone's made is correct - at your income levels, you should get the full 20% QBI deduction, which on $23,500 would be up to $4,700 in additional deduction. That's significant money! Since your deadline is approaching, focus on getting your Schedule C completed first (your tutoring income and any business expenses), then the QBI deduction will flow from there. You've got this!

Great advice in this thread! One additional consideration for @ApolloJackson - since you mentioned this was your primary residence before becoming a rental, make sure you understand the depreciation recapture rules. If you claimed depreciation deductions during those 2 years when it was a rental property, you'll need to "recapture" that depreciation and pay taxes on it at a rate up to 25% (rather than capital gains rates). This recapture happens regardless of whether you use installment sale treatment - it's required to be recognized in the year of sale. Only the capital gain portion above the depreciation recapture can be spread out over the installment payments. Your CPA will be able to calculate this for you, but it's something to factor into your tax planning since it could affect your 2025 tax liability even though you're receiving payments over 15 years. Also, keep excellent records of all maintenance, improvements, and expenses related to the property during your ownership - these can help reduce your overall taxable gain!

This thread has been incredibly informative! As someone new to this community but dealing with a similar situation, I wanted to add a few practical tips from my recent experience with owner-financing. First, definitely keep meticulous records from day one. I created a simple filing system with folders for: the original sales contract, promissory note, payment records, and tax documents. Each monthly payment gets logged with date received, amount, and the principal/interest breakdown. Second, consider setting up automatic payments if possible - it makes tracking easier and ensures consistent cash flow. I use a separate bank account just for these transactions, which simplifies record-keeping and makes it obvious what's investment income versus other sources. Finally, regarding the tax software limitations others mentioned - I found that even premium versions of popular tax software struggle with owner-financing scenarios. Having your amortization schedule prepared before tax season (either from the tools mentioned here or created yourself) will save you headaches later. @ApolloJackson - sounds like you're on the right track planning ahead! The fact that this was your former residence definitely adds complexity with the potential Section 121 exclusion and depreciation recapture, so having all your documentation ready for your CPA will be key.