This is a really helpful thread! Just wanted to add one more thing that might be useful - make sure your son and his girlfriend both keep good records of which expenses they're paying for each child. Things like medical bills, daycare costs, school supplies, etc. If they're each claiming one child, the IRS could potentially ask for proof that they're actually providing more than half the support for their respective claimed child. Also, they should probably sit down together and formally decide who claims which child going forward, rather than just assuming. Having it in writing (even just a simple agreement between them) can help avoid confusion later and shows they're being intentional about following the rules rather than just randomly splitting the kids.

This is such a practical question that comes up a lot! Just want to emphasize something that others touched on - the "residency test" is really crucial here. Each parent needs to make sure the child they're claiming actually lived with them for more than half the year (more than 183 days). Since they're doing 50/50 custody, they'll need to be really careful about tracking this. Even a few extra days can make the difference in who's eligible to claim which child. I'd suggest they keep a shared calendar or app where they track exactly which nights each child stays at each house - not just for tax purposes, but it's also great for co-parenting coordination. One more tip: if either parent is eligible for the Earned Income Tax Credit (EITC), that can be a significant benefit too. The amount varies based on income and number of qualifying children, so they might want to run some scenarios to see how different arrangements could affect their overall tax situation.

Has anyone here actually gone through the process of acquiring one of these GSA lighthouses? The application requirements seem intense, and I'm wondering how competitive the process is. Are there usually multiple nonprofits applying for each lighthouse?

One thing to keep in mind with the GSA lighthouse program is that you'll need to demonstrate significant financial capacity upfront. These properties often require substantial immediate repairs - we're talking potentially $100K+ just to make them safe and weather-tight before you can even think about B&B operations. The GSA will want to see your nonprofit has either cash reserves or committed funding sources for initial restoration work. If you're planning to rely on rental income from the for-profit business to fund maintenance, you'll need a very detailed financial projection showing how you'll handle the gap between acquisition and when rental income begins. Also worth noting - lighthouse properties are typically quite remote with limited utilities infrastructure. Factor in costs for upgrading electrical, plumbing, and septic systems to handle B&B operations. These expenses need to be part of your nonprofit's budget since the property will be owned by the 501(c)(3). The good news is that successfully operating lighthouses as B&Bs can be quite profitable given their unique appeal, but the upfront investment is substantial and the nonprofit needs to be financially prepared for that reality.

Just to give a different perspective - I tried doing my S-Corp taxes with TurboTax Business last year and deeply regretted it. Spent 20+ hours struggling through it, thought I'd done everything right, and still got notices from the IRS about missing forms 6 months later. Had to hire a CPA to fix everything anyway and ended up paying way more than if I'd just gone to them in the first place.

As someone who's been through the exact same transition from W-2 to S-Corp, I'd definitely recommend going the CPA route for your first year. The complexity isn't just in filing the returns - it's understanding all the ongoing compliance requirements that TurboTax won't teach you. Since you mentioned you've only been taking owner's draws instead of paying yourself a salary, you're going to need professional help to sort that out anyway. The IRS is pretty strict about S-Corp owners paying themselves reasonable compensation through payroll, and getting that wrong can trigger audits or penalties. One thing I wish someone had told me: start interviewing CPAs now, not in March when everyone's swamped. Many good ones are already booking up for tax season. Look for someone who specializes in small business and can explain things clearly - you want to learn the process, not just hand everything off blindly. The investment in professional guidance your first year will save you headaches (and probably money) down the road. Once you understand the S-Corp requirements and have proper systems in place, you can always consider doing simpler years yourself later.

This is a really common confusion! I had the exact same worry when I hired someone on Fiverr for graphic design work last year. The key thing to remember is that as an individual consumer (not a business), you don't have any 1099 filing obligations at all, regardless of the amount you spend. The $600 threshold that your accountant friend mentioned only applies to businesses paying independent contractors directly. Since you paid through Fiverr's platform, they handle all the tax reporting responsibilities. Fiverr will issue appropriate forms (like 1099-K) to sellers who meet their reporting thresholds. Your situation is no different from buying something on Amazon or eBay - you're a consumer making a purchase through a marketplace platform. The platform manages the tax obligations between themselves and their sellers. You can focus on your own tax prep without worrying about issuing any forms to the artist!

This thread has been incredibly helpful! I was in almost the exact same situation - commissioned artwork through Fiverr for about $650 and my tax preparer mentioned the 1099-NEC requirement. I was panicking thinking I'd have to somehow get the artist's SSN or EIN to file forms. Reading through everyone's explanations really clarified the difference between being a business paying contractors directly versus being a consumer using a marketplace platform. The key distinction seems to be that platforms like Fiverr act as the middleman and handle all the tax reporting obligations themselves. I feel much more confident going into tax season now knowing I don't need to worry about issuing any forms for my Fiverr purchases. It's reassuring to see so many people had similar concerns and got confirmation from various sources (IRS agents, tax software, etc.) that individual consumers don't have these filing requirements when using third-party platforms.

Don't forget that as a sole proprietor you can deduct half of your self-employment tax on your 1040! It's an adjustment to income so you get it even if you don't itemize deductions. A lot of people miss this one.

As someone who went through this exact same situation last year (RN with a photography side business), I totally get the confusion! Here's what I learned the hard way: The key is understanding that your W2 withholding might already be covering more than you think. Don't just look at raw percentages - you need to consider your effective tax rate across both income streams. One thing that helped me was doing a "tax projection" using Form 1040ES worksheets instead of relying on online calculators. Take your expected total income from both sources, subtract your standard deduction, and calculate the tax on that amount. Then subtract what's already been withheld from your nursing paychecks to see what you actually still owe. Also, make sure you're maximizing business deductions! As a personal trainer, you can likely deduct equipment, continuing education, professional liability insurance, mileage to clients, and even a portion of your phone bill if you use it for business. These deductions can significantly reduce your taxable business income. The 35% you're setting aside is probably conservative, which is good! Better to overpay and get a refund than underpay and face penalties. But you might find you need less once you factor in all legitimate deductions.