2 Have your partner look into filing as HoH if they're claiming your child. That would give them a better tax break than filing as single. Also check if either of you qualify for Earned Income Credit depending on your income - that could make a big difference!

You're absolutely correct that you cannot file as Head of Household in this situation. Since your boyfriend claims your son as a dependent, you don't have a qualifying person to meet the HoH requirements, even though you may be paying a significant portion of household expenses. Your boyfriend, however, likely qualifies for HoH filing status since he claims your child as a dependent and presumably pays more than half the cost of maintaining the household (this would need to include his portion of mortgage, utilities, plus the health insurance and other expenses he covers). For next year, you might want to consider whether it makes financial sense to alternate who claims your son, but you'd need to run the numbers carefully. The person claiming the child must be providing more than half of the child's support, so you'd need to track all expenses related to your son specifically (not just household expenses) to see if this arrangement would work and benefit your family overall. Also worth noting - make sure your boyfriend is indeed filing as HoH if he qualifies, as it provides better tax rates and a higher standard deduction compared to Single filing status.

11 I'm confused about something slightly different but related. If my LLC is taxed as an S-Corp and I pay myself a salary, should I just reimburse myself for the business portion instead of having the business pay the full bill?

Great question! I've dealt with this exact situation in my consulting business. You have two main approaches: **Option 1 (Most Common):** Have your business pay the full phone bill, then split it in your bookkeeping - 50% goes to "Telephone Expense" (deductible) and 50% goes to "Owner's Draw/Distribution" (non-deductible personal expense). **Option 2:** Pay the bill personally and have your business reimburse you only for the 50% business portion. For documentation, you don't need to track every single call. A simple log for one representative month showing your business vs. personal usage pattern is usually sufficient. Or keep a written statement explaining how you determined the 50% (like "I use my phone roughly half the time for customer calls, scheduling, and business communications"). The key is being consistent with your method and having reasonable documentation to back up your percentage if the IRS ever asks. Make sure whatever approach you choose, you stick with it throughout the year for consistency.

Wait, I'm confused about the timing. If the kid lived with you for 15 months, that means they lived with you for all of last year plus a few months of the previous year, right? So you DEFINITELY qualify under the residency test (which requires 6+ months). Did you provide more than half their support too? Food, clothing, shelter, medical, etc?

The 15-month timeline definitely works in your favor for the residency test! Since your niece has been living with you for over a year, you clearly meet the requirement that the child lived with you for more than half the tax year. For a niece to qualify as your dependent, she needs to meet either the "qualifying child" or "qualifying relative" tests. As your niece, she can be a qualifying relative if: (1) she lived with you all year OR is related to you (which she is), (2) her gross income was less than the exemption amount ($4,400 for 2023), (3) you provided more than half her total support, and (4) she's not filing a joint return with someone else. The swing from owing $3k to getting a $1,900 refund makes perfect sense - that's likely the Child Tax Credit and possibly the Additional Child Tax Credit kicking in, which can be worth up to $2,000 per qualifying child. Your processing delay is almost certainly just the IRS being overwhelmed rather than any red flags. Returns with refundable credits (especially involving dependents) routinely take longer to process because they undergo additional verification. The fact that you filed exempt on your W-4 shouldn't impact your dependent claim at all - these are completely separate determinations.

I've been running a mountain biking blog for 2 years now. Here's what I learned: track EVERYTHING! I use a spreadsheet where I log every expense with: date, amount, category, business %, and purpose. I take photos of all receipts. For travel, I document each day with what content I created. The IRS cares most about your INTENT - if you can show you genuinely intend to make profit (even if you don't right away), you're in better shape.

As someone who's been through several IRS audits for my freelance consulting business, I can tell you that documentation is absolutely everything. For your travel blog situation, the key is proving business intent from day one. Here's what I'd recommend: Before you leave, create a detailed business plan showing projected revenue streams (affiliate marketing, sponsored posts, product sales, etc.). Document your content creation schedule and upload timeline. Keep a daily log during travel noting what business activities you performed each day (filming, writing, networking with other creators, etc.). For expenses, you can typically deduct the business percentage. So if 30% of your trip days involve significant content creation, you might deduct 30% of accommodation costs for those specific days. The laptop and camera are easier - if used 80% for business, deduct 80%. One critical point: don't wait to start monetizing. Set up affiliate accounts, Google AdSense, and sponsor outreach before you leave. Having these revenue streams active (even if earning pennies) shows the IRS you're serious about profit, not just enjoying a subsidized vacation. The "profit in 3 of 5 years" rule gives you breathing room, but having some revenue from year one makes your case much stronger.

Just a tip: Make sure to update your address with the county tax assessor's office after you pay off your mortgage! I didn't do this and my tax bill went to my old mortgage company. Almost missed the payment deadline and would have incurred penalties. Usually there's a form on your county's website for this.

One thing that helped me when I went through this was to contact my county tax office in advance to let them know I'd be taking over direct payments. They were able to set up automatic notifications so I wouldn't miss the November deadline. Also, if your county offers online payment options, I'd recommend setting that up early - it's much easier than mailing checks and you get instant confirmation receipts that work perfectly for tax documentation. Some counties even let you set up payment reminders via email or text. The transition from lender-managed to self-managed property tax payments is smoother when you're proactive about it!