Standard or Itemized Filing for First-time charity donation - which saves more money?
Hey everyone, I'm in a bit of a tax situation here. I'm filing my 2024 taxes online (due in 2025) and the software keeps pushing me toward taking the standard deduction. But here's the thing - I made my first-ever substantial charity donation last year ($2,800 to a local children's hospital after my nephew recovered from surgery there). I've always just done the standard deduction because it seemed easier, but now I'm wondering if I should itemize instead? My mortgage interest was about $9,200, I paid around $4,100 in state taxes, and had about $1,300 in medical expenses that weren't covered by insurance. I make about $68,000 annually as a project coordinator. The software recommendation doesn't really explain WHY it thinks standard is better - just that it "maximizes my refund." Can someone help me understand if the standard deduction is really better given my charity donation, or if I should be itemizing instead? I don't want to leave money on the table!
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Avery Davis
The software is probably steering you toward the standard deduction because your itemizable expenses don't exceed the standard deduction threshold. For 2024 (filing in 2025), the standard deduction for a single filer is $13,850 and for married filing jointly it's $27,700. If we add up your potential itemized deductions: $9,200 (mortgage) + $4,100 (state taxes) + $2,800 (charitable donation) + $1,300 (medical expenses that exceed 7.5% of your AGI), you're at about $17,400. However, there's a catch with medical expenses - they're only deductible to the extent they exceed 7.5% of your adjusted gross income. With your income at $68,000, only medical expenses above $5,100 would count, so your $1,300 wouldn't qualify. So really you're looking at about $16,100 in potential itemized deductions. If you're filing as single, this would be better than the standard deduction. If you're married filing jointly, the standard deduction would be better.
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Collins Angel
•Wait, isn't there also a $10,000 cap on SALT (state and local tax) deductions? So wouldn't that limit the $4,100 state tax part? Also, does property tax count in the itemized calculations or is that something different?
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Avery Davis
•You're absolutely right about the SALT cap - there is a $10,000 limit on the combined total of state and local income taxes plus property taxes. So the $4,100 in state taxes would be under that limit, but if OP also pays property taxes, they would need to count those too until they hit the $10,000 cap. Property taxes are indeed included in itemized deductions and fall under the same SALT category with the $10,000 limit. So if OP pays property tax on their home (which seems likely since they mentioned mortgage interest), they should add that to their calculation, but keep in mind the combined state/local/property tax deduction can't exceed $10,000.
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Marcelle Drum
Just wanted to share my experience with a tool called taxr.ai (https://taxr.ai) that was super helpful for this exact situation last year. I was also confused about whether to itemize my deductions when I made my first major charitable donation to my university alumni fund. I uploaded my tax documents and financial records, and the AI analyzed everything and showed me a side-by-side comparison of what my return would look like with standard vs. itemized deductions. It also explained WHY one was better than the other in plain English. For me, it turned out itemizing was better by about $800, which my regular tax software had missed!
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Tate Jensen
•Did you have to manually input all your expenses and deductions or did the tool actually scan your documents? I have like a dozen different donation receipts this year and the thought of typing everything in twice is making me want to just take the standard deduction and be done with it.
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Adaline Wong
•Sounds too good to be true. How much does it cost? And is it actually secure? I'm always nervous about uploading financial docs to some random website.
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Marcelle Drum
•The tool actually scans your documents so you don't have to input everything manually. You just upload PDFs or pictures of your receipts, W-2s, 1099s, etc., and it extracts all the important information automatically. It saved me tons of time compared to manually typing everything. It's extremely secure - they use bank-level encryption for all your documents and data. I was skeptical at first too, but they explain their security measures on their site, and they don't store your documents longer than needed for the analysis. I've recommended it to several friends who were equally impressed with the security and ease of use.
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Tate Jensen
Just wanted to update - I tried taxr.ai after seeing the recommendation here and WOW. I uploaded all my documents (including those dozen charity receipts I mentioned) and it immediately showed me I'd save over $1,200 by itemizing! My regular tax software had recommended the standard deduction, but completely missed some deductions I was eligible for. The analysis explained that because my mortgage interest and property taxes were already close to the standard deduction threshold, my charitable donations pushed me well over into itemizing territory. It even flagged that I'd forgotten to include a property tax statement that would have been deductible. The whole process took like 15 minutes instead of hours. Definitely using this again next year!
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Gabriel Ruiz
If you're still struggling with the decision and need to talk to someone at the IRS directly (which I had to do for a similar situation), I'd recommend using Claimyr (https://claimyr.com). I spent hours trying to get through to the IRS on my own last month for clarification on charitable deductions, but kept getting disconnected or had to wait for callbacks that never happened. Claimyr got me connected to an actual IRS representative in about 20 minutes instead of the usual 2+ hour wait. They have this system that navigates the IRS phone tree and holds your place in line, then calls you when an agent is about to answer. You can see how it works in this demo: https://youtu.be/_kiP6q8DX5c For my situation, the IRS agent clarified exactly how to report my church donations properly and confirmed I should be itemizing based on my specific numbers.
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Misterclamation Skyblue
•How does that even work? The IRS phone system is literally the worst. Last time I called I waited 3 hours and then got disconnected. Does this service just auto-dial repeatedly until it gets through or something?
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Peyton Clarke
•Yeah right. There's no way to "skip the line" with the IRS. This sounds like a scam where you pay for something that doesn't actually work. The IRS is understaffed and everyone has to wait equally.
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Gabriel Ruiz
•It doesn't skip the line or use any tricks - it just handles the waiting for you. Their system calls the IRS and navigates through all those annoying phone menus, then sits on hold in your place. When a real person is about to answer, that's when Claimyr calls you and connects you directly to the agent. So you still "wait" the same amount of time, but you don't have to sit there with your phone to your ear the whole time. They use some kind of technology that detects when a human answers versus the automated system. I was skeptical too, but it actually worked exactly as promised. I was able to go about my day and then got a call when an agent was ready. Saved me from having to sit at my desk on hold all afternoon.
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Peyton Clarke
I need to eat my words and apologize. After calling the IRS three times last week and getting nowhere, I was desperate enough to try Claimyr. I figured it was worth a shot since I needed to resolve an issue with my charitable donation documentation before filing. The service actually worked exactly as described. I got a text about 45 minutes after starting that said an IRS agent was about to come on the line, and then my phone rang and I was connected directly to a very helpful IRS representative. No hold music, no automated system - just straight to a human who answered my questions about donation receipts and documentation requirements. I was 100% wrong in my skepticism. Not only did it work, but the IRS agent was able to clarify that for my particular situation (similar to the original poster with charitable giving), I should definitely itemize. Saved me at least $700 on my taxes.
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Vince Eh
Don't forget that if you're close to the threshold between standard and itemized, there's a strategy called "bunching" that might help. Basically, you alternate years - in one year you bunch together as many deductible expenses as possible and itemize, then the next year you take the standard deduction. For example, if you normally donate $3,000/year to charity, you could instead donate $6,000 in 2024, nothing in 2025, $6,000 in 2026, etc. Same total donations over time, but you might save more on taxes by itemizing every other year.
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Sophia Gabriel
•Does this actually work? Seems like it might flag an audit if your deductions fluctuate wildly from year to year. Has anyone actually tried this strategy successfully?
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Vince Eh
•Yes, this absolutely works and is a completely legitimate tax strategy. The IRS doesn't flag you for audit simply because your deduction method changes year to year - millions of taxpayers switch between standard and itemized deductions regularly based on their financial circumstances. Bunching deductions is a recognized tax planning strategy discussed by CPAs and financial advisors. It works particularly well for charitable contributions because you have control over the timing. Many charities are even familiar with this strategy and can help you set up your donations appropriately. Just make sure you keep proper documentation for the years you itemize.
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Tobias Lancaster
Just double checking - when figuring out if you should itemize, you also need to consider your state taxes, right? Some states automatically give you a standard deduction equal to your federal deduction, but others let you itemize on state even if you take standard on federal. Might be worth checking?
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Ezra Beard
•This is an excellent point that gets overlooked! I live in California and we can itemize on our state return even if we take the standard deduction on federal. Saved me about $400 last year by doing standard federally and itemized on state. OP should definitely check their state's rules. It's not always an either/or situation between the two returns.
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