Pro tip: Always make copies or scan important tax documents before sending anything to the IRS! I learned this the hard way years ago. Now I have a digital folder for each tax year with scans of all my documents.

I've been through this exact situation! Don't worry too much - the postal service will almost certainly return your envelope to you marked "postage due" or "return to sender." It usually takes about 3-7 business days depending on your location. While you're waiting for it to come back, I'd recommend taking these steps right away: 1) Contact your employer's HR or payroll department TODAY and request duplicate W-2s. Tell them it's urgent due to the tax deadline - most companies can reissue them within a few days. 2) If you have your final paystub from December, that contains most of the same information as your W-2 and can help you get started on preparing a backup return. 3) Consider switching to e-filing for this year once you get your documents sorted out. It's much safer, faster, and you get immediate confirmation that the IRS received your return. The good news is you still have time before the deadline, and this happens to more people than you'd think! Just don't wait around - start working on getting those replacement documents now so you're ready to file as soon as possible.

Has anyone used a third-party service to help with the ERO application? I'm in a similar boat and wondering if it's worth hiring someone or if I should just apply directly.

I actually went through this exact situation about 2 years ago with a DUI from 6 years prior. I was terrified that it would prevent me from getting ERO status, but it turned out to be much less of an issue than I expected. The key things that helped me were: 1) Being completely honest on Form 8633 - I disclosed everything upfront, 2) Including a brief letter explaining the circumstances and what I learned from the experience, and 3) Emphasizing my clean record and professional conduct since then. My application was approved without any follow-up questions. The IRS seems much more concerned with recent issues or patterns of behavior rather than isolated incidents from several years ago. Your 9 years of experience as a tax preparer with an active PTIN actually works strongly in your favor - it shows you've been trusted with tax preparation responsibilities and maintained good standing. Don't let the DUI stop you from pursuing your business goals. Just be honest, provide complete information, and let your professional track record speak for itself.

I'm wondering what tax software people use for reporting this kind of income? I've always just used the free SimpleTax/Wealthsimple Tax but not sure if it handles self-employment stuff well?

One thing I haven't seen mentioned yet is the importance of keeping detailed records from day one. Since platforms like feetfinder handle payments digitally, make sure you're downloading monthly statements and keeping screenshots of your earnings. The CRA can ask for proof of income going back several years if they ever audit you. Also, don't forget about potential business deductions! If you're using your phone for photos, a portion of your phone bill might be deductible. Same with internet costs, any props or clothing you buy specifically for photos, even a portion of your home if you're using a specific room for photo shoots. These deductions can help offset some of the tax burden. I'd also recommend opening a separate bank account just for this income if you're planning to take it seriously. Makes tracking so much easier come tax time, and it looks more professional if the CRA ever has questions.

I'm just starting my S Corp journey too and this thread has been incredibly helpful! I was literally panicking yesterday when my accountant handed me a similar list of vendors who need 1099s. One thing I'm still confused about - if I paid someone like $400 in cash for makeup services throughout the year but then also Venmo'd them $300 for additional work, does that $700 total mean they need a 1099? Or since the Venmo portion might be handled by the payment processor, do I only count the cash payments toward the $600 threshold? Also, for those of you who've been through this process - how far back do you typically keep records of these vendor payments? I'm trying to organize everything for this year but also wondering if I should be worried about prior years before I had the S Corp set up. Thanks for sharing all your experiences - it's making this whole learning curve feel way less intimidating!

I'm dealing with this exact same situation right now! Just set up my S Corp last month and my accountant dropped the same bombshell about 1099s. Reading through all these responses has been super educational. One thing I'm still trying to wrap my head around - how do you all handle vendors who work both personal and business services? Like my makeup artist does my everyday look but also does special event makeup for professional appearances. Do I need to track and separate those payments, or can I treat all payments to her as business expenses since I'm in entertainment? Also, seeing the penalties mentioned here ($50-$280 per form) is definitely motivating me to get this right from the start. Better to be overprepared than deal with IRS headaches later. Thanks everyone for sharing your experiences - this community has been way more helpful than trying to decode IRS publications on my own!

Don't stress too much about this! I accidentally selected "retail" for my SAAS business two years ago and it's never caused any issues. The business category on the EIN application isn't as critical as people make it out to be. The IRS cares more about accurate income reporting than the specific category you select during application.

Great question! I went through this exact same process last year for my SaaS startup. After researching extensively and consulting with my accountant, I selected "Service" for our EIN application. The reasoning is that SaaS businesses are fundamentally providing ongoing access to software functionality rather than selling a tangible product. Even though customers "purchase" subscriptions, what they're really buying is continuous access to your service platform. This puts it squarely in the service category rather than retail, which is typically reserved for businesses selling physical goods or one-time software purchases. The IRS views subscription-based software access as a service offering, similar to how they'd classify other subscription services like consulting or cloud hosting.