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I know this is slightly off topic from the exemption card, but has anyone else noticed that some online retailers don't charge sales tax even when they're supposed to? Not complaining obviously, but wondering if this is legal or if they're just breaking the rules?
That's actually a great question. Following the Supreme Court's South Dakota v. Wayfair decision in 2018, states can require online sellers to collect sales tax even without physical presence in the state. However, many states have small seller exemptions - if a business has fewer than a certain number of transactions or sales below a threshold amount in that state, they may not be required to collect tax. But if you're seeing larger retailers not collecting tax, they might be non-compliant. Keep in mind that even if they don't collect it, technically you're supposed to report and pay use tax on those purchases when you file your state tax return (though very few people actually do this). It's definitely a gray area that's still evolving in enforcement.
Just to add some context to all the great information here - I work in state tax compliance and wanted to clarify a few things about sales tax exemptions. The diplomatic cards mentioned earlier are indeed real and legitimate, but they're very specific to foreign diplomatic personnel under international treaties. For regular citizens, the most common legitimate exemptions are actually medical-related. Many states offer sales tax exemptions on prescription medications, medical devices, and sometimes even over-the-counter items if you have certain qualifying conditions. Some states also have exemptions for clothing under a certain dollar amount or during specific tax-free weekends. If you're curious about what exemptions you might qualify for, your state's Department of Revenue website usually has a comprehensive list. It's much more limited than what diplomats get, but there are legitimate ways to reduce your tax burden without needing special cards!
This is really helpful information! I had no idea about the medical exemptions. Do you know if there's a standard list of qualifying medical conditions across states, or does each state set their own rules? I have diabetes and wondering if my test strips and supplies might qualify for exemptions that I've been missing out on.
Is there any expiration on capital loss carryovers? I've been carrying some for almost 4 years now.
Nope! Capital losses can be carried forward indefinitely until they're used up. I've been carrying some losses for over 6 years now.
One thing I'd add to the great advice already shared - make sure you're applying your capital loss carryover in the correct order! The IRS requires you to use the oldest carryover losses first (FIFO - first in, first out). Since you had a $20,000 loss in 2022, that entire amount should be applied against your 2023 gains before you can use any losses from 2023 itself. This shouldn't affect your calculation (you'll still net $30,000), but it's important for record-keeping purposes. Also, double-check that you actually filed your 2022 return and properly reported that $20,000 loss. If for some reason it wasn't properly documented on your 2022 Schedule D, you might run into issues when the IRS processes your 2023 return. The carryover amount needs to have a paper trail from your previous filing.
Great point about the FIFO rule! I didn't know about that requirement. Quick question - if I had losses in both 2021 and 2022, do I need to apply the 2021 losses first even if I already used some of them in previous years? I'm trying to make sure I track everything correctly for my upcoming filing.
Has anyone here actually succeeded in itemizing with Healthshare expenses? We're on Samaritan and paying about $750/month in shares plus had about $5k in expenses that weren't shared this year. But we're still well below the standard deduction threshold for married filing jointly.
We managed to do it last year, but only because we had a perfect storm of deductible expenses. Between our Liberty Healthshare costs, massive property taxes, mortgage interest on our new house, and some large charitable donations, we cleared the standard deduction by about $3k. Saved us around $600 in taxes. This year we'll probably be back to taking the standard deduction though.
Thanks for sharing your experience. It's helpful to know it's possible but requires a lot of other deductions too. I think we'll stick with the standard deduction based on our situation, but I'll keep better records this year just in case we get close.
Based on my experience with Healthshares and tax law, I want to clarify a few key points that might help you navigate this situation: First, you're correct that your monthly Healthshare contributions ($8k annually) are NOT the same as traditional insurance premiums for tax purposes. However, they DO count as qualifying medical expenses when calculating your itemized deductions, subject to the 7.5% AGI threshold. The $9k you paid out-of-pocket that wasn't reimbursed is also deductible as medical expenses. So you'd have $17k in potential medical deductions ($8k contributions + $9k out-of-pocket), which exceeds your 7.5% threshold of approximately $12,750 (based on $170k income). However, the reimbursed $29k is NOT deductible, regardless of whether you paid providers first and got reimbursed later. The IRS looks at the final economic burden - if you were ultimately made whole through reimbursement, you can't deduct those expenses. Given your income level and the amounts involved, you'd need to carefully calculate whether itemizing would benefit you over the $27,700 standard deduction for married filing jointly. Include your medical expenses above the threshold, state/local taxes (up to $10k), mortgage interest, and charitable donations to see if itemizing makes sense. Keep detailed records of everything, including dates, amounts, and proof of payment/reimbursement. Healthshare arrangements can sometimes trigger additional IRS scrutiny, so documentation is crucial.
This is exactly the kind of detailed breakdown I was hoping for! Your explanation really helps clarify the distinction between what counts as medical expenses versus what's actually deductible after reimbursements. One thing I'm still wondering about - you mentioned that Healthshare arrangements can trigger additional IRS scrutiny. Is there anything specific we should be prepared for if we do end up itemizing? Should we be keeping any particular types of documentation beyond the usual receipts and statements? Also, with our other potential deductions (property taxes, charitable giving, etc.), we might actually get close to that $27,700 threshold. It sounds like it's worth running the numbers both ways to see which option saves us more money.
Have you called the Treasury Offset Program directly? Sometimes they have more info than the state does. Their number is 800-304-3107. You'll need your ex's SSN and your case number.
I went through this exact same situation in Massachusetts last year! The waiting is absolutely brutal, especially when you're counting on that money. Here's what I learned from my experience: The 4-8 week timeline is pretty accurate, but it can stretch longer during tax season. Mine took about 7 weeks total. What really helped me was keeping a log of every call I made and who I spoke with - it made follow-up calls way more productive. One thing nobody mentioned yet is that you should ask the MA DOR for the "offset notification letter" - this shows the exact amount that was sent from the federal government and when. If there's a discrepancy between what you expect and what you receive, this letter is crucial. Also, if you haven't already, make sure your address is current with both the IRS and MA DOR. I've seen cases where payments get delayed because they're sent to old addresses. The waiting sucks but hang in there - the money will come through!
This is really comprehensive advice, thank you! I never thought about asking for the offset notification letter - that's brilliant. I'm definitely going to request that when I call tomorrow. The address thing is a good point too, I moved about 6 months ago and want to make sure everything is updated. It's reassuring to hear from someone who actually went through this process in MA and got their money eventually!
Cass Green
This entire discussion has been incredibly helpful! I'm dealing with a hybrid situation where my business does both product sales and services, so I've been completely confused about when to use Form 1125-A versus just putting everything on Schedule C. Reading through everyone's experiences, I think I finally understand the key distinction. For my business, I sell handmade jewelry (physical products with inventory) AND offer custom design consultations (pure service). For the jewelry side, materials like silver wire, beads, clasps, and even the small jewelry boxes I put finished pieces in would go on Form 1125-A since they're directly incorporated into the final products I sell. But my design software subscription, business cards, website hosting, and consultation fees would all be Schedule C operating expenses. Melina's "100 more units" test is perfect for this - if I made 100 more necklaces, I'd need 100 more sets of materials and packaging, but I wouldn't need 100 times more website hosting or business insurance. The real lightbulb moment for me was Yara's point about service businesses often not needing Form 1125-A at all. For my consultation work, there's no inventory or direct production costs, so those revenues and related expenses stay entirely on Schedule C. Thank you everyone for sharing your real-world examples - this has been way more helpful than any official IRS publication I've tried to read!
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Zoey Bianchi
ā¢Your hybrid business situation is exactly what I'm dealing with too! I run a small bakery where I sell both pre-made items (cookies, muffins) and custom cakes for events. Reading your jewelry example really helped me think through my own categorization issues. For my pre-made items, ingredients like flour, sugar, eggs, and packaging boxes would be Form 1125-A costs since they directly go into each product. But for custom cake consultations and design work, those would be pure service revenue on Schedule C with related expenses like design software and client meeting costs. The "100 more units" test is going to be my go-to from now on - it's so much clearer than trying to parse the technical IRS language. If I baked 100 more cookies, I'd need proportionally more ingredients and packaging, but my commercial kitchen rent and business license fees would stay the same. Thanks for breaking down your hybrid approach - it's reassuring to know other businesses face this same complexity and that there's a logical way to think through it!
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Lucas Bey
This has been such an enlightening discussion! As someone who just started a small business this year, I was completely overwhelmed by Form 1125-A and had no idea what qualified for Line 5 "Other Costs." The real-world examples from Melina's furniture business and Cass's jewelry/consultation hybrid really drove home the core concept for me. I keep coming back to that "100 more units" test - it's such a practical way to distinguish between direct production costs (Form 1125-A) and general operating expenses (Schedule C). What I found most valuable was learning that many service-based businesses don't even need Form 1125-A at all. I was stressing about this form for my tutoring business, but since I don't have any physical inventory or raw materials, all my expenses (books, supplies, software subscriptions) just go on Schedule C as regular business expenses. For anyone else feeling overwhelmed by this form, I'd definitely recommend starting with the inventory question that several people mentioned: Do you track raw materials or finished goods from year to year? If not, you might be able to skip 1125-A entirely and focus on properly categorizing expenses on Schedule C instead. The documentation point from CyberSiren about keeping detailed records is also crucial - especially if you do have legitimate "Other Costs" for Line 5. The last thing anyone wants is an audit because of unclear expense categorization!
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