Hey, tax preparer here (though not your tax preparer). Just to clarify something important: the 1099-K threshold changed for 2025 filing season! For 2024 taxes (that you file in 2025), payment apps and services must issue 1099-Ks when transactions exceed $5,000. This is a big change from the previous $20,000 threshold. For delivery drivers specifically, you should receive a more detailed annual summary from the app companies that breaks down: - Total amount charged to customers (what's on 1099-K) - Restaurant/merchant payments (not your income) - Your actual earnings (base pay + tips through the app) Use these detailed statements when filing Schedule C, and keep them with your tax records!

Just wanted to share my experience as someone who went through this exact confusion last year. I'm a rideshare driver and got hit with multiple 1099-Ks that made it look like I earned way more than I actually did. The key thing I learned is that you absolutely need to get the detailed earnings statements from each app - not just the 1099-K. For example, my Uber 1099-K showed $15,000, but my actual driver earnings were only about $9,500 after you subtract the rider payments that just passed through to Uber's booking fees, tolls, etc. I ended up working with a tax professional who specializes in gig workers, and they showed me how to properly report this on Schedule C. You report your actual earnings (not the inflated 1099-K amount), then deduct your business expenses like mileage, phone bills, car washes, etc. The mileage deduction alone saved me hundreds. One tip: if you use multiple apps, make sure you're not double-counting miles driven. I was tracking total miles and trying to claim them for each app, which would have been incorrect. You can only deduct the actual business miles once, even if you had multiple apps running. For cash tips, I keep a simple log in my phone's notes app - just date and rough amount. Most gig workers I know report the majority of their cash tips but not necessarily every single dollar, and that seems to be the practical reality of the situation.

One thing nobody mentioned yet - if your brothers self-employment income is really small (like under $400 net profit) he doesn't have to pay self-employment tax on it, but still has to report the income. Saved me some $$$ when I was just starting my side gig!

Another important thing to consider is recordkeeping! For your brother's freelance work, he needs to track EVERYTHING - receipts, mileage, client payments, business equipment purchases, even home office expenses if he works from home. The IRS requires good documentation for all business deductions. I learned this the hard way when I couldn't find receipts during an audit. Now I use a simple spreadsheet or app to track expenses monthly rather than scrambling at tax time. For mixed-use expenses like his phone or internet, he'll need to calculate the business percentage based on actual usage. The key is being able to prove the business purpose if ever questioned. Also, since he has both W-2 and 1099 income, he should definitely consider making quarterly estimated tax payments for the freelance portion. The IRS expects you to pay taxes throughout the year, not just at filing time, and there can be penalties if you owe too much in April.

This is such a helpful thread! I'm dealing with a similar situation where I want to gift some Nvidia shares to my grandson for his college fund. Based on what everyone's shared here, it sounds like I should definitely use specific identification to choose which shares to transfer rather than just defaulting to FIFO. One question though - does the timing of when I actually execute the gift matter for tax purposes? Like if I set up the transfer in December but it doesn't complete until January, which year does it count for gift tax purposes? And does that affect which tax year my grandson would report any gains if he sells them relatively quickly? Also really appreciate the mentions of taxr.ai and Claimyr - going to check both out since my broker (Schwab) has been just as unhelpful as Vanguard was for the OP!

Just wanted to add something that might help with your Vanguard situation - I had a similar experience where customer service wouldn't explain the tax implications, but I found their online resource center actually has some decent explanations about cost basis methods for gifts and transfers. The key thing to understand is that when you gift shares, you're essentially passing along your "tax history" with those shares to your niece. The cost basis method you select determines exactly which shares (with their specific purchase dates and prices) get transferred. Since you've held these tech stocks for 7 years, you probably have multiple "tax lots" purchased at different times and prices. FIFO (which you selected) means you're giving away your oldest shares first. This could be good or bad depending on whether those early purchases were at higher or lower prices than your more recent ones. If the stock price has generally gone up over those 7 years, FIFO would transfer your lowest-cost-basis shares, meaning higher potential capital gains for your niece when she sells. For future reference, "specific identification" gives you the most control - you can literally pick and choose which exact shares to transfer based on what's most tax-advantageous for your niece's situation. But since you already completed the transfer, don't stress too much about it. The main thing is that you documented everything properly for both your records and hers.

I've been reading through everyone's experiences here and I'm amazed at how helpful this community is! I'm dealing with a similar situation - filed in early March and still waiting on my $2,850 refund. Like many others, I've been calling randomly with no success, but after seeing all these detailed strategies, I realize I've been doing everything wrong. I had no idea about checking transcripts first or that specific error codes could explain delays. The consistency of success with the 7AM Tuesday/Wednesday approach combined with Omar's phone sequence is really encouraging. I'm planning to check my transcript tonight and set my alarm for 6:55 AM Tuesday. It's frustrating that we have to become IRS code experts just to get our own money, but at least now I have a real plan instead of just dialing and hoping. Thank you everyone for sharing what actually worked - this thread has given me more useful information than months of googling!

Welcome to the community! I'm new here too but have been dealing with a similar refund nightmare - filed in January and still waiting on my $3,200 refund. Reading through everyone's experiences has been incredibly eye-opening. Like so many others, I've been randomly calling with zero success, but now I realize I was doing everything completely backwards. The transcript-first approach that everyone keeps mentioning makes total sense - going in armed with actual error codes instead of just saying "where's my refund" seems like the key difference between success and failure. I had no idea these specific codes even existed or that they could explain exactly what's causing delays. I'm definitely going to follow the winning strategy from this thread: check my transcript tonight, set alarm for 6:55 AM Tuesday, and use Omar's phone sequence with the SSN trick. It's absolutely ridiculous that we have to become IRS code experts just to get our own money back, but at least now I have a real plan instead of just dialing and praying. Thank you everyone for sharing what actually worked - this community has been more helpful than months of frustrated googling! Will definitely update with results after trying the Tuesday morning approach.

I'm a bookkeeper and see this issue all the time. Here's a simpler way to approach capex calculation from Schedule L: 1. Calculate the change in gross fixed assets (End - Beginning): $14.3M - $10.5M = $3.8M 2. Calculate the change in accumulated depreciation: $6.5M - $9.1M = -$2.6M 3. The negative change in accum. depreciation means assets were disposed of 4. True capex = Change in gross assets + Value of disposed assets The tricky part is finding the value of disposed assets. Look at Form 4797 for this info, or you can estimate by looking at the details of which asset classes changed. Also, don't forget to subtract any non-cash acquisitions like equipment acquired through business combinations or leases newly capitalized.

This is why I hate Schedule L. The instructions are so vague!!! I spent like 3 hours on this last night and still couldn't figure it out. Has anyone used TurboTax Business for this? Does it automatically calculate capex or do I still need to manually figure this out? I dont want to spend $170 on the software if it doesnt even help with this.