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Ask the community...

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Zara Ahmed

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Make sure you're keeping a detailed spreadsheet of all transactions! I had a similar issue with my eBay 1099-K last year and got audited because my deductions seemed high compared to my reported income. I had to prove every single purchase with receipts. Screenshots of your StubHub purchase history won't be enough if you get audited - you need actual receipts or credit card statements showing what you paid for each ticket.

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What kind of organization system did you use? I've got hundreds of ticket transactions and I'm not sure how to best organize everything in case of an audit.

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I use a Google Sheets template with columns for: Date, Event, Purchase Price, Purchase Receipt/Confirmation #, Sale Price, Sale Date, StubHub Fees, Net Profit/Loss. Then I have a separate folder in Google Drive where I store PDFs of all my receipts and confirmation emails, named with the same confirmation numbers from my spreadsheet. The key is matching each purchase to its corresponding sale so you can prove your cost basis. I also keep a running total at the bottom that should match my 1099-K minus fees. Takes a bit of time to set up initially, but it's saved me so much stress during tax season!

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Lauren Wood

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I went through this exact same situation with my concert ticket reselling last year! The panic is totally understandable when you see that 1099-K amount, but you're definitely on the right track thinking about deductions. One thing I learned the hard way - make sure you're treating this as a business from the start. Since you're already making regular sales and have business expenses, the IRS will likely view this as a business activity rather than occasional personal sales. This means Schedule C is probably the right approach. A few practical tips: Start organizing your records NOW while it's still fresh. Create a simple spreadsheet matching each ticket purchase to its sale - this will be crucial if you ever get audited. Also, don't forget about the StubHub seller fees that get deducted from your payouts - those are deductible business expenses too. For TurboTax, look for the "Business Income and Expenses" section and select Schedule C. It will walk you through entering your 1099-K income and then guide you through the expense categories. Your ticket costs go under "Cost of goods sold" and things like gas, fees, and subscriptions go under regular business expenses. You've got this! The key is just being thorough with your documentation.

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Yuki Ito

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This is such helpful advice! I'm just getting started with ticket reselling myself and hadn't thought about treating it as a business from day one. Quick question - when you mention matching each purchase to its sale, what do you do if you bought tickets in bulk (like season tickets) but sold them individually throughout the year? Do you need to calculate a per-ticket cost basis for each individual sale? Also, did you end up having to make quarterly estimated tax payments once you established this as a business? I'm worried about getting hit with penalties if I don't plan ahead properly.

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Quick tip that most people miss: keep track of ALL medical-related mileage! Every mile driving to doctors, pharmacies, treatments, etc. is deductible at 22 cents per mile for 2024. Doesn't sound like much but it adds up fast if you had lots of appointments.

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Eli Butler

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I tried claiming medical mileage last year and my tax software flagged it as an "audit risk" item. Is there some specific way we're supposed to document this? Do we need anything beyond a personal log of trips?

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For medical mileage documentation, the IRS doesn't require anything super complex, but you do need to keep a written record. A simple log showing the date, destination (doctor's office, pharmacy, etc.), purpose of the trip, and miles driven is sufficient. You can use a notebook, smartphone app, or even a spreadsheet. The key is being consistent and contemporaneous - don't try to recreate months of trips from memory at tax time. Many people use apps like MileIQ or even just the notes app on their phone to track this. Your tax software flagging it as "audit risk" is probably just because it's a commonly overlooked deduction that sometimes gets inflated. As long as you have proper documentation and reasonable mileage amounts, you should be fine. The IRS expects people to claim legitimate medical travel expenses.

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Max Reyes

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Just wanted to add one more thing that might help - make sure you're tracking any over-the-counter medications that were prescribed by your doctor! A lot of people don't realize that OTC meds like aspirin, allergy medicine, or pain relievers can be deductible if your doctor specifically recommended or prescribed them. You'll need documentation showing the doctor's recommendation (like a note in your medical records or a written prescription), but it's another way to boost your medical expense total. I discovered this when going through my bills and found several OTC items my cardiologist had recommended that I completely forgot about. Also, don't forget about medical equipment like blood pressure monitors, glucose meters, heating pads, or anything else your doctor recommended for treatment. These all count toward your medical expenses too!

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Just fyi there's a huge difference between community property states and non-community property states when it comes to step-up basis for surviving spouses!!! My mom got a full step-up on ALL assets when my dad died because they lived in California (community property state), but my aunt who lives in new york only got step-up on my uncle's half of their joint assets. Cost her like $30k more in taxes when she sold their vacation home!!!

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This is super important. The community property states are: Arizona, California, Idaho, Louisiana, Nevada, New Mexico, Texas, Washington and Wisconsin. If you're in one of these, you get full step-up on community property when a spouse dies. Everywhere else, only the deceased spouse's portion gets stepped up.

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Amara Okafor

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Just want to emphasize what others have said - you're absolutely fine and caught this at the perfect time! I went through almost the exact same situation when I inherited my grandfather's portfolio last year. One additional tip: make sure you get proper documentation of the December death date value. If these were publicly traded stocks, you can usually pull historical price data from sites like Yahoo Finance or your brokerage. For the exact date of death value, you'll typically use either the closing price on that date, or if you want to be more precise, you can use the average of the high and low prices for that day. Also keep in mind that if your grandmother died on a weekend or holiday when markets were closed, you'd use the closing price from the next trading day. The IRS is pretty reasonable about this stuff as long as you have documentation and use a consistent method. You're going to save yourself a lot of money by reporting this correctly - that $66,000 difference in taxable gains is huge! Props for doing your research before filing.

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Has anyone used turbotax to file the form 5695? Do they make it easy to enter these home improvement credits or should I use a tax professional next year?

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I used TurboTax last year for Form 5695 and it was pretty straightforward. They have a section specifically for energy credits with questions that walk you through what qualifies. Just make sure you have all your documentation ready before you start - receipts, manufacturer certifications, contractor statements about energy efficiency, etc.

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Thanks for the insight! That's reassuring to hear it's manageable through TurboTax. I'll definitely gather all my documentation beforehand as you suggested. Most importantly I'll get the contractor to break out the insulation costs separately on the invoice.

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Dylan Fisher

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Great question! Yes, the 3/8" insulation board should qualify for the energy efficiency credit on Form 5695 under line 18 for "Insulation or air sealing material or system." The key is that it needs to be primarily installed for energy efficiency purposes, which it sounds like yours is. A few important points to maximize your credit: 1. **Get itemized documentation**: Definitely ask your contractor to break out the insulation materials and installation costs separately on the invoice. Don't estimate - having clear documentation is crucial if the IRS ever reviews your return. 2. **R-value documentation**: Make sure your contractor includes the R-value of the insulation boards on the invoice or in a separate statement. This helps prove it meets energy efficiency standards. 3. **Installation photos**: Take photos during installation showing the insulation boards before the siding goes on top. This provides visual proof of the work. 4. **Credit limits**: You're right that the credit maxes out at $1,200 (30% of up to $4,000 in qualifying costs), so even a moderate insulation cost will likely max it out. The vapor barrier function is secondary - as long as the primary purpose is insulation for energy efficiency, you should be good to claim it. Just make sure all your documentation clearly identifies this as an insulation upgrade rather than just a siding project.

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Yuki Ito

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Do actors pay taxes differently from musicians and athletes? Like if Taylor Swift makes $20 million from a tour vs an actor making $20 million from a movie, do they pay the same amounts?

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Carmen Lopez

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Musicians often have more complex income streams than actors. They earn from touring, merchandise, streaming, publishing rights, etc. Each can be taxed differently. Athletes deal with "jock taxes" where they pay taxes in EVERY state they play games in! So yeah, very different situations even at similar income levels.

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Andre Dupont

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Musicians also have to split income with bandmates, managers, labels, and producers. Most famous musicians actually make way less per project than famous actors do. James Taylor once said that on streaming platforms, he needs about 50,000 plays to make the same money as selling ONE album CD. The tax situation is brutal for musicians.

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CosmicCadet

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The tax situation for high earners like Chris Hemsworth is fascinating but varies greatly based on how they structure their income. While someone making $20 million would face the top federal tax bracket of 37%, their actual effective rate depends heavily on deductions and business structures. Most A-list actors don't receive traditional W-2 wages. Instead, they often create loan-out corporations or LLCs that contract their services to studios. This allows them to deduct legitimate business expenses like agent/manager fees (which can total 25-30% alone), security, training, travel, and other work-related costs. Additionally, income timing matters. Actors might defer portions of their pay or structure deals with backend participation that spreads income across multiple years, potentially keeping them in lower brackets for some portions. Even with aggressive (but legal) tax planning, a $20 million earner would likely still pay $5-8 million in total federal and state taxes. The key difference is they have access to sophisticated tax strategies that most people don't, which is why their effective rates are often lower than the headline marginal rates suggest.

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