Quick question for anyone who knows - if I have multiple 1099-DIVs from different brokerages, and several have amounts in Box 5, do I just add all those Box 5 amounts together for Form 8995? Or do I need to list them separately somehow?

I had the same confusion last year with my Vanguard 1099-DIV! The good news is that with your $95K income, you're well below the threshold where things get complicated, so you'll use the simple Form 8995. TurboTax should automatically prompt you for Form 8995 when you enter the Box 5 amount from your 1099-DIV, but sometimes you need to make sure you're in the right section. When you're entering your dividend income, look for a question about "Section 199A dividends" or "qualified business income from investments." The 20% deduction on your Box 5 amount can be pretty substantial - I saved about $150 last year just from my mutual fund dividends. Make sure you don't skip over it! If TurboTax isn't automatically including it, you might need to upgrade from the free version to access Form 8995.

mine came yesterday actually! took exactly 2 weeks from when i filed. check ur mailboxes yall

This is exactly why I always check for any processing issues before filing. H&R Block should have notified clients about this upfront - it's pretty frustrating to find out after the fact that your refund timeline just got extended by 1-2 weeks. At least now we know what's going on though. Thanks for sharing this info!

3 Something nobody's mentioned yet - keep a mileage log if you drive as part of your caregiving duties! I deducted over $2,000 last year just from tracking my mileage driving my client to doctor appointments and running errands for them. The IRS mileage rate for 2025 is 65.5 cents per mile.

One important thing to consider is whether you should be classified as a household employee versus self-employed. Since the family is claiming you on their taxes for a dependent care credit, they might actually be required to treat you as a household employee and handle payroll taxes. If you're a household employee, they should be withholding and paying Social Security and Medicare taxes on your behalf. However, if you control how and when you work (set your own schedule, use your own supplies, etc.), you're likely self-employed. For $15,300 in annual income, you'll definitely want to make quarterly estimated tax payments to avoid penalties. I'd recommend setting aside at least 25-30% of each payment to cover both self-employment tax and income tax. Don't forget you can deduct legitimate business expenses like mileage, supplies, and any training related to caregiving. You should also check if the family needs to provide you with any tax documents - they may need to give you information for their dependent care credit claim even if they don't issue a 1099.

I'm in a similar situation but we solved it by having all beneficiaries make small annual contributions to the trust for "maintenance fees." It's way below market rate rent, but our attorney said it helps establish that we're not just getting completely free use which could be viewed as distributions.

This is a complex area where the facts really matter. Based on what you've described, the trust paying for basic property maintenance expenses (taxes, utilities, insurance) on property it owns would typically be considered trust expenses rather than distributions to beneficiaries. The trust is maintaining its own asset. However, the free use of the property by beneficiaries could potentially create imputed income issues. The IRS could argue that the fair rental value of your usage represents a distribution to you. This is especially true if the usage is significant or if certain expenses are more "personal" in nature (like premium cable packages). Key considerations: Does your trust document explicitly allow beneficiary use without compensation? How many days per year does each beneficiary use the property? Are there any expenses that are clearly for beneficiary convenience rather than property maintenance? I'd strongly recommend having your trustee consult with a tax attorney who specializes in trust taxation. The $28,000 annual expense level makes this worth getting right, and the stakes are high enough that professional guidance would be money well spent.

14 Don't overthink this too much! I've been selling art at shows for years. I use my brand name on my W-9, but I've never formally registered it. The main thing is that you report all your income on your taxes. If you're a sole proprietor, it all goes on your Schedule C anyway.

Great discussion here! As someone who just went through this process myself, I'd recommend checking your state's specific DBA requirements before making any decisions. In my state, using a business name without registration is fine for tax purposes, but I ran into issues when trying to open a separate business bank account later. One thing that really helped me was creating a simple spreadsheet to track all my art-related income and expenses from day one, regardless of what name I use on forms. This makes tax time much easier whether you're operating under your legal name or a brand name. Also, don't forget that even if you use a DBA on your W-9, you'll still need to use your legal name and SSN as the primary taxpayer information. The business name is just additional identification for their records.