Has anyone mentioned the option of paying medical providers directly? If you pay the hospital or doctors directly instead of giving money to your sister/niece, those payments don't count against your annual gift tax exclusion. This is especially important if you're collecting $250k-$500k from family.

This is such a thoughtful way to help your niece during her recovery. I went through something similar when my nephew had a serious motorcycle accident a few years ago. One thing I learned that might be helpful - if you're looking at collecting that much money from family ($250k-$500k), you definitely want to coordinate who's paying what directly to medical providers vs. giving cash gifts. The unlimited medical exclusion only applies when payments go directly to qualified medical providers, not when you reimburse family members. Also, since you mentioned your niece might have ongoing recovery needs, consider timing these payments strategically. Medical expenses paid in different tax years can help spread out any gift tax implications for family members who might exceed the annual exclusion limits. Make sure to keep detailed records of everything - who paid what, when, and to which providers. This documentation becomes really important if anyone in your family ends up needing to file gift tax returns. The IRS will want to see clear proof that payments were for qualified medical expenses if you're claiming the unlimited medical exclusion. Hope your niece recovers quickly and completely!

PRO TIP: your transcript will tell you way more than WMR. Go pull those if you can access them

I feel your pain! Been in the exact same situation - filed in late January as Head of Household and got stuck with that same "delayed beyond normal timeframe" message for what felt like forever. The worst part is how vague they are about timelines. From my experience, the Head of Household status does seem to trigger extra reviews more often. They want to make sure you actually qualify (supporting a qualifying person, paying more than half the household costs, etc.). I ended up having to wait about 8 weeks total before it finally moved to "Refund Approved" and then got deposited within a few days after that. The key thing is that once you see that delay message, you're basically in a manual review queue. No amount of checking the app will speed it up unfortunately. I know it's frustrating but try to check maybe once a week instead of daily - it'll save your sanity and your phone battery! 😅 Hang in there, it will eventually process!

I've been dealing with similar Fidelity 1099-B confusion for years! One thing that really helped me understand these "Proceeds Investment Expenses" was realizing they often correspond to expense ratios or management fees that got deducted from ETFs or mutual funds throughout the year. Since you mentioned SLV ETF specifically, this could be related to the expense ratio being collected. ETFs typically have their expense ratios deducted by selling tiny fractional shares periodically rather than as a separate fee. This is why you see zero quantity transactions but still have proceeds - they're selling microscopic amounts to cover the ongoing fund expenses. The good news is that this is all handled automatically in terms of cost basis adjustments. When you eventually sell your SLV position, your cost basis will already reflect these fee collections, so you don't need to do any manual calculations. For tax reporting, just enter these exactly as they appear on your 1099-B. Most tax software will handle these routine transactions correctly once you input the data from the form.

I just went through this exact same situation with my Fidelity account last month! Those "Proceeds Investment Expenses" transactions really threw me for a loop initially. What helped me understand it was looking at my monthly statements more carefully. Fidelity sometimes collects certain fees (like foreign transaction fees on international ETFs, or reorganization fees) by automatically selling tiny fractional shares rather than debiting cash from your account. This is especially common if you don't have enough cash balance to cover small fees. The key thing to remember is that even though you didn't initiate these sales, they're still reportable transactions for tax purposes since shares were actually sold to generate the cash for the fees. The IRS expects to see these reported since Fidelity sends them a copy of your 1099-B. One tip: if you want to avoid these micro-transactions in the future, try keeping a small cash balance in your account so Fidelity can debit fees directly rather than selling shares. But for this tax year, just report everything exactly as it appears on your 1099-B - the tax software should handle it correctly.

Has anybody used care.com or similar services for finding backup childcare? I'm wondering if using an agency vs hiring directly affects the tax deduction situation at all.

One thing to keep in mind is that your irregular 1099 schedule might actually work in your favor for justifying these additional childcare expenses. Since you can't predict when you'll be called in for those 14+ hour shifts or overnight assignments, having backup childcare available becomes a legitimate necessity for maintaining your income. The key is documentation - keep a detailed log of your work calls/assignments and how they correlate with your childcare needs. This will help support your claim that the nanny/au pair expenses are directly tied to your ability to work, especially during times when regular daycare isn't available (evenings, weekends, extended hours). Also consider that with your unpredictable schedule, you might qualify for a higher percentage of the Child and Dependent Care Credit if your irregular income puts you in a lower AGI bracket. The credit percentage can be up to 35% of qualifying expenses for lower income levels.

I'm surprised no one has mentioned this, but if you're ONLY concerned about sharing your SSN with this new manager guy, could you just mail/fax a completed W-9 form directly to their accounting department instead of giving it to him personally? That way you're still providing what they legally need, but limiting who has access to your personal info.

I've been in this exact situation before and understand your concerns about privacy. Here's what I learned: as a single-member LLC owner, you actually have some flexibility in how you handle this. The key issue is that since your payments were made to your personal name rather than your business name, the company is technically correct in requesting your SSN for the 1099. However, you do have options: 1. **For 2024 payments already made**: You can explain to them that you operate under a business entity and request they use your EIN instead of SSN, along with your business name. Some companies will accommodate this request. 2. **For future payments**: Definitely transition to having checks made out to your business name, then provide your EIN for those transactions. 3. **Privacy protection**: If you must provide your SSN, consider Effie's suggestion about mailing the W-9 directly to their accounting department rather than giving it to the new manager. The most important thing is that regardless of which number appears on the 1099, all income still gets reported on your personal tax return via Schedule C since your LLC is disregarded for tax purposes. The 1099 is just an information document - it doesn't change your actual tax obligations. If the company pushes back, you might want to get clarification from a tax professional about your specific situation and rights as an LLC owner.