I'm in a similar situation with my triplex and wanted to share what I learned from my CPA last year. One key thing not mentioned yet is the "exclusive use" test for your personal residence unit. Make sure you're not accidentally claiming deductions for shared spaces like hallways, basements, or common areas that you use personally - these can't be allocated to rental units. Also, for the family-occupied units, consider having your parents pay for their own utilities separately if possible. This helps establish a clearer business relationship and makes the rental nature more defensible if questioned. Even if they're not paying rent, having them cover their own electric/gas bills creates better documentation. One more tip: if you're doing significant renovations, take detailed before/after photos and keep all receipts organized by unit. During tax season, this makes the repair vs improvement determination much clearer, and it's invaluable if you ever face an audit.

I've been managing rental properties for over a decade and wanted to add a few important points that might help: For your renovation expenses, document everything with contractor invoices that clearly separate labor from materials. The IRS often looks more favorably on repairs when you can show you were fixing specific problems rather than just upgrading. For example, "replaced water-damaged subfloor and matching laminate" reads very different from "installed new luxury vinyl plank flooring." Regarding your parents' units, there's actually a middle ground option many people miss: you could establish a "services in lieu of rent" arrangement. If they're genuinely providing property maintenance and childcare services, document the fair market value of those services and treat it as if they're paying rent equal to that value, then you're paying them for services. This requires careful documentation but can make those units qualify as rental property for tax purposes. One critical point about the insurance deduction - make sure you're not double-counting. If you're deducting insurance as a rental expense for the rental unit, you can't also claim it as part of your homeowner's deduction on Schedule A. The IRS catches this overlap frequently. Finally, consider setting up a separate business checking account for all property-related expenses, even for your primary residence portion. It makes record-keeping much cleaner and shows the IRS you're treating this seriously as a business operation.

As someone new to this community, I have to echo what Emma and Aurora have said - you're potentially walking into a legal minefield here. I've been researching similar situations after seeing friends get into trouble with payment processors and regulatory agencies. One aspect that hasn't been fully explored is the streaming platform's terms of service. Many platforms have specific rules about financial transactions conducted through their services, and facilitating gambling with viewer money could violate their terms even if it's technically legal in your jurisdiction. Also, consider the liability issues - if someone claims you lost their money unfairly or if there are technical issues during a stream that affect the gambling outcomes, you could face civil lawsuits. Without proper business structure and potentially insurance, you're personally liable for any disputes. The tax complexity alone should be a red flag. Even if you're just "passing through" money, the IRS will want documentation proving the flow of funds, and any mistakes in reporting could trigger audits or penalties that cost more than whatever entertainment value this provides. I'd strongly suggest stepping back from this activity until you can consult with professionals who specialize in gaming law and business formation. The risks here extend far beyond just tax reporting.

As a newcomer to this community, I'm genuinely concerned after reading through all these responses. The legal and financial risks everyone has outlined are extensive and serious - from potential money transmitter violations to gaming law issues to platform terms violations. What strikes me most is how what seemed like a simple streaming concept has so many different regulatory pitfalls. The fact that multiple experienced members are independently raising red flags about federal law violations, state gambling regulations, and personal liability issues should be a major wake-up call. @KingKongZilla - I really hope you take the advice here seriously about consulting with gaming law and tax attorneys before continuing. The consensus seems clear that this activity could expose you to risks far beyond what any entertainment value or tips could justify. Even if you've been doing this for a while without issues, that doesn't mean you're in the clear - regulatory enforcement can happen at any time, and the consequences could be life-changing. It might be worth exploring completely different streaming content that doesn't involve handling other people's money for gambling. There are so many successful streamers who build audiences without taking on these kinds of legal and financial risks.

This is such a helpful thread! I'm a new single-member LLC owner (started my graphic design business 3 months ago) and was completely confused about the W9 situation. Reading through everyone's experiences has been really reassuring. I've been doing exactly what the original poster described - personal name on line 1, business name on line 2, using my SSN - but I was second-guessing myself when clients started asking questions about payment processing. It's good to know this is the correct approach. The idea of creating an educational document to send with W9 forms is genius! I'm definitely going to put together something similar. Has anyone found that getting an EIN later (even as a single-member LLC) caused any complications with existing client relationships, or is it pretty straightforward to transition mid-year if you decide to go that route? Also really appreciate the practical tips about invoice wording - small details like that can prevent so much confusion down the line.

Great thread! As someone who's been running a single-member LLC for 4 years now, I can confirm that all the advice here is solid. I wanted to add one more perspective that might help newcomers avoid some pitfalls I experienced. When I first started, I made the mistake of being inconsistent with how I presented my business information to different clients. Some got W9s with just my personal name, others got the full LLC setup, and it created a mess during tax season. The key is consistency - pick one approach (personal name + business name + SSN like you're doing) and stick with it for ALL clients. Also, I've found it helpful to have a brief conversation about payment processing during the initial client onboarding. I explain upfront that I'm a single-member LLC taxed as a sole proprietor, so payments can go to either name, but the important thing is using the correct tax ID. Most clients appreciate the transparency and it prevents awkward conversations later when they're trying to cut checks. One last tip: keep really good records of which clients paid using which name format. Even though the IRS systems can handle it, having your own documentation makes tax prep much smoother and gives you confidence if any questions come up later. A simple spreadsheet tracking client, payment method, and name used has saved me hours during tax season.

Based on previous filing seasons, I've noticed PA refunds follow a pattern. Early filers (January) typically see 3-4 week turnaround. Peak season filers (February-March) experience 5-7 week waits. Late filers often receive refunds faster, sometimes in just 2-3 weeks. This matches what happened in 2022 and 2023. The system seems designed to handle the largest volume in the middle of tax season.

Just got my PA refund yesterday! Here's my timeline: • Filed: February 1, 2024 • Status changed to "Processing": February 3 • Status changed to "Under Review": February 17 • Status changed to "Approved": March 12 • Direct deposit received: March 14 Total time: 42 days from filing to deposit. Hope this helps give you a concrete example!

23 Has anyone here used TurboTax to handle the PSO health insurance exclusion? I'm wondering if it has a specific input for this or if I need to somehow manually adjust my income to account for it.

12 Great discussion here! As someone who went through this exact situation a few years ago, I wanted to add that it's also worth keeping detailed records of your health insurance premium payments throughout the year, even though they're being deducted directly from your pension. The IRS could potentially ask for documentation during an audit to verify that the excluded amount was actually used for qualifying health insurance or long-term care premiums. I keep copies of my insurance statements showing the monthly premium amounts, plus documentation from my pension administrator showing how much was deducted each month. Also, don't forget that this exclusion applies to both health insurance AND qualified long-term care insurance premiums, up to the combined $3,000 limit. Some retired officers miss the long-term care piece and could be excluding more if they have both types of coverage.