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I'm confused about something... if the client wrote checks directly to the subcontractors but asked you to deliver them, would you still need to file 1099s? Asking because I'm in a similar situation but my client wrote checks with the sub names on them, I just handed them out.
Great question! If the client wrote checks DIRECTLY to the subcontractors (with the subs' names as payees), then the client would be responsible for filing the 1099s, not you. The key is whose name is writing the payment to whom. In your case, since the client wrote checks directly to the subs, you were just the messenger. You don't need to issue 1099s for those payments. But for the original poster, since they received money from the client and then wrote their own checks to the subs, they're considered the payer and need to issue the 1099s.
Just want to emphasize one important detail that might save you headaches - make sure you get W-9 forms from ALL your subcontractors before you pay them, not after. I made the mistake of trying to collect tax info after the job was done and some contractors had already moved on to other cities or changed phone numbers. Also, keep detailed records of everything - copies of all checks you wrote, the amounts, dates, and what work each contractor did. If you get audited, the IRS will want to see the paper trail showing these were legitimate business expenses. Since you're reporting this on Schedule C, having good documentation will help justify the deductions and show you weren't just trying to hide income. One more tip: if any of your contractors were incorporated businesses (like "ABC Roofing LLC"), you generally don't need to send them 1099s. But you still need to report the expenses on your Schedule C.
This is really solid advice about getting W-9s upfront! I learned this lesson the hard way on a smaller project last year. One contractor I paid $800 to just disappeared after the job - no working phone number, nothing. I ended up having to do backup withholding documentation and it was a nightmare. The incorporated business tip is huge too. I almost sent a 1099 to a roofing company that was clearly an LLC, which would have been unnecessary paperwork. Quick question though - how do you usually verify if a contractor is incorporated? Do you just ask them or is there a way to look it up?
Just wondering - has anyone had issues with their refund after filing a superseding return? I'm in a situation where I'd get a bigger refund with the corrected return and wondering if it complicates or delays things?
I went through this exact same situation two years ago and can confirm what others have said about the process. One thing I'd add that saved me a lot of stress - when you write "SUPERSEDING RETURN" at the top, use a red pen or marker if you're mailing it in. It makes it much more visible to the processors. Also, keep copies of EVERYTHING. I mean your original return, the superseding return, all your supporting docs, and even the envelope you mail it in (take a photo). The IRS processed mine correctly, but having all that documentation gave me peace of mind. One more tip - if you're close to the deadline, send it certified mail with a return receipt. That way you have proof it was delivered before April 15th, which is crucial since superseding returns must be filed by the original deadline.
This is incredibly helpful advice, especially about using a red pen! I never would have thought of that detail but it makes total sense. The certified mail tip is also smart - I was planning to just use regular mail but you're right that having proof of delivery before the deadline could be really important. Quick question - when you say keep copies of everything, do you mean I should make copies before I mail the superseding return, or are you talking about keeping the originals and sending copies? I want to make sure I don't accidentally send something I need to keep.
As someone who just went through this exact same maze of confusion last tax season, I completely feel your pain! The cost basis calculations for multiple stock purchases can be absolutely overwhelming, especially when your broker doesn't provide the basis information. Your Amazon example is spot-on with the FIFO calculation - you're correct that it would be $1,235 cost basis ($650 for the first 5 shares + $585 for 3 of the second batch). Unfortunately, as others have mentioned, you can't choose the method that gives you lower taxes after the fact. Since you didn't specify which shares to sell at the time of the transaction, you're stuck with FIFO. One thing that saved my sanity was creating a simple "lot tracking" spreadsheet with columns for Purchase Date, Shares, Price Per Share, and Total Cost. When I sold shares, I just worked from the oldest purchases down until I accounted for all shares sold. This visual approach made the FIFO method much clearer than trying to do it all in my head. Also, definitely double-check your broker's online portal for additional transaction details that might not be on your printed 1099-B - I found dividend reinvestment records there that I had completely missed initially. Those small DRIP transactions can really add up and significantly impact your cost basis calculations. The manual process is painful but educational. Next year, consider setting up specific identification with your broker if you want more control over tax optimization. Hang in there - it gets much easier once you establish a good tracking system!
As a newcomer to this community and investment taxes in general, I wanted to thank everyone for this incredibly detailed and helpful discussion! I'm in almost the exact same situation as Carter - first time dealing with stock transactions on my taxes and completely confused about cost basis calculations. The clarification that FIFO is mandatory for individual stocks (unless you specified shares at sale time) was crucial for me to understand. I had been hoping I could just pick whichever method gave me lower taxes, but now I see why that's not allowed. What I find most valuable about this thread is how many different approaches and tools have been shared - from manual spreadsheet tracking to automated platforms like taxr.ai, to professional CPA review services. It gives newcomers like me options based on our comfort level and complexity of our situations. I'm planning to follow the systematic approach several people recommended: start with the manual Publication 550 method to learn the fundamentals, then use an automated tool to verify my calculations. The emphasis on downloading complete transaction histories (including those easy-to-miss dividend reinvestments) before starting seems absolutely critical. One question for the group: for someone with about 15-20 stock transactions in their first year, would you still recommend the manual approach first, or at that volume should I jump straight to one of the automated tools to avoid potential calculation errors? I'm reasonably comfortable with spreadsheets but definitely want to get this right. Thanks again to this amazing community for sharing such detailed experiences and practical advice!
Has anyone dealt with a situation where the deceased owner hadn't been taking depreciation properly before death? My uncle passed and left me his rental property, but I discovered he hadn't claimed depreciation for 3 years even though he should have. Does the step-up basis just make all that irrelevant now?
Yes, the step-up in basis essentially wipes the slate clean. Your uncle's failure to take depreciation (even though he was entitled to it) becomes irrelevant once you receive the stepped-up basis at date of death. You start fresh with the new basis and depreciation schedule. That's actually one of the nice benefits of the step-up rules for heirs.
Great question about the depreciation situation! I went through something very similar when my grandmother passed and left me her duplex. She had also missed claiming depreciation for several years before her death. The good news is that @Libby Hassan and @Eva St. Cyr are absolutely right - the step-up in basis at death essentially gives you a clean slate. All the missed depreciation from before becomes irrelevant because you're starting with a fresh basis equal to the fair market value at the date of death. One thing I'd add is that you might want to consider filing an amended return for your uncle's estate if the missed depreciation deductions were significant. While it doesn't affect your stepped-up basis, it could result in refunds for the estate that the beneficiaries would receive. My CPA helped us recover about $4,200 in missed deductions from my grandmother's final three years. Also, make sure to start your depreciation schedule immediately once you inherit - don't repeat your uncle's mistake! The IRS expects you to claim depreciation whether you actually take it or not, so there's no benefit to skipping it.
That's really helpful information about potentially amending the deceased's returns! I hadn't considered that angle. Quick question - is there a time limit for filing those amended returns for missed depreciation? And does it complicate things if the property has already been transferred to beneficiaries and then to an LLC like in the original post? I'm asking because I'm wondering if @Levi Parker might want to look into this for their situation too, since they mentioned the original owner took proper depreciation in 2019-2020 but who knows about earlier years.
Fiona Gallagher
For what it's worth, the American Opportunity Tax Credit does require that the student be enrolled at least half-time and be pursuing a degree. So they do need verification of enrollment status, but not grades. The Form 8863 that's used for education credits doesn't ask for GPA or individual course performance. Your parents just need documentation that you're enrolled in a qualifying educational institution. The 1098-T plus an enrollment verification letter is more than sufficient.
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Ayla Kumar
ā¢Thank you for this specific information! I've gone ahead and requested an enrollment verification letter from my registrar's office. I'm going to offer them that plus remind them they already have the 1098-T. Hopefully that resolves things without further conflict.
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Emma Thompson
Your instincts are absolutely right - this is not a legitimate tax requirement. I've been doing taxes for families for over a decade, and transcripts with grades are never needed for any IRS education credit or deduction. What your parents actually need for tax purposes: - Form 1098-T (which shows tuition paid) - Receipts for qualified education expenses like required textbooks - Enrollment verification showing you're at least half-time (for dependency and education credit purposes) The IRS doesn't care about your GPA for the American Opportunity Credit, Lifetime Learning Credit, or any education deductions. They only care that you're enrolled and that qualifying expenses were paid. I'd recommend getting an enrollment verification letter from your school's registrar (usually free or very low cost) and offering that along with pointing out they already have the 1098-T. If they keep insisting on the transcript after that, then you know this is really about checking your grades, not taxes. At that point, it becomes a family boundary discussion rather than a tax compliance issue. Stand your ground on this - you're not being unreasonable at all.
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Javier Torres
ā¢This is exactly what I needed to hear! As someone new to dealing with taxes and family boundaries, I was starting to second-guess myself. Your breakdown of what's actually required versus what my parents are asking for is super helpful. I'm definitely going to follow your advice about getting the enrollment verification letter. It sounds like that plus the 1098-T should cover all legitimate tax needs. If they still push for the transcript after that, at least I'll know for sure this isn't really about taxes. Thank you for validating that I'm not being unreasonable - sometimes it's hard to tell when you're in the middle of family drama!
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