Dumb question but do personal checks from clients who didn't send 1099s count as "under the table" income? My tax guy said i don't need to report income without a 1099 but that sounds wrong to me.

This is exactly the kind of mixed income situation that trips up a lot of freelancers! The good news is that having personal reimbursements mixed with business income in your bank account isn't inherently problematic - you just need to be able to document the difference. Here's what I'd recommend: Create a simple spreadsheet with three columns - Date, Amount, and Type (Business Income vs Personal Reimbursement). Go through your bank statements and categorize each deposit. For the reimbursements like your dad's utility bills or friend payments, keep any supporting documentation (texts, emails, original receipts) that show these were reimbursements rather than income. The IRS cares about accuracy, not perfection in your banking setup. As long as you can substantiate which deposits were actual income versus personal transactions, you'll be fine. That said, definitely consider opening a separate account for future business income - it makes everything so much cleaner come tax time. One last thing - make sure you're setting aside money for quarterly estimated tax payments if you haven't been doing that already. Self-employment tax can be a nasty surprise if you're not prepared!

All of this back filing info is helpful but just be aware there are time limits on claiming refunds! If you're owed money from the IRS, you typically have only 3 years from the original due date to file and claim a refund. So for example, for tax year 2020 (which was due April 2021), you have until April 2024 to file and still get your refund. For 2017, the deadline to claim a refund was April 2021 - if you're filing 2017 now, you can still file the return but you wouldn't get any refund you were owed. Just wanted to mention this since it seems like some people are discussing filing returns from several years back!

Just wanted to chime in as someone who went through this exact situation last year. I was trying to back file for 2018 and got so much conflicting information from different sources that I almost gave up. The bottom line is: NO tax software can e-file returns for prior years beyond what the IRS accepts (current year + maybe previous year early in filing season). This is an IRS system limitation, not a software limitation. Both TaxACT and TurboTax will let you prepare old returns online, but you'll have to print and mail them. I ended up using TaxACT because it was cheaper for prior years ($25 vs TurboTax's $60), but the end result was identical - had to mail everything in. One tip: make sure you use certified mail when sending old returns. The IRS processing times for mailed returns can be really long (took 4 months for mine), and you want proof they received it. Also double-check you're mailing to the correct address for your state - it's different than where you'd mail current year returns. Good luck with your 2017 filing!

I've been using FreeTaxUSA for 5 years now. The state returns are usually available by mid-January, sometimes earlier depending on your state. For your estimated payment, you can probably just use the same method you used for Q3 unless your income has changed significantly.

I made the switch from TurboTax to FreeTaxUSA two years ago and it was one of my best financial decisions! A few tips for your transition: 1. **State returns timing**: California forms are usually available by late January, but you're right to be concerned about the January 15th deadline. I'd recommend calculating your estimated payment based on your Q3 method or using 110% of last year's tax liability to be safe. 2. **Data entry**: Since this is your first year with FreeTaxUSA, gather all your previous tax documents beforehand. The interface is clean and intuitive, but you'll need to manually enter everything this first time. 3. **Features you might miss**: FreeTaxUSA doesn't have some of TurboTax's bells and whistles like the mobile app for document photos, but honestly, I found those features more gimmicky than useful. 4. **Import capabilities**: You can import W-2s and 1099s directly from most major employers and financial institutions, which saves a ton of time. The $15 state fee is still a steal compared to what TurboTax was charging me ($120+ for state). You'll love not being constantly upsold to premium versions you don't need!

Just wanted to share something important that bit me last year. If you use the trailer for personal use AT ALL, you need to track the percentage of business vs personal use. Section 179 deduction gets reduced proportionally. So if you use that dump trailer 80% for business and 20% for personal projects, you can only deduct 80% of the cost under Section 179. Keep a log of usage if there's any chance of personal use - dates, job sites, clients, miles, etc. Solid documentation is crucial if you ever get audited!

Great question about the Section 179 deduction! I actually went through this exact situation with my landscaping business last year when I bought a used skid steer. The good news is that used equipment absolutely qualifies for Section 179 as long as it meets the requirements - which it sounds like your dump trailer will. A few key points to keep in mind: Make sure you have solid documentation of the purchase price and business use percentage. Since you mentioned it'll be used 100% for business, that's perfect. Also, consider the timing - the equipment needs to be "placed in service" (actually used in your business) by December 31st to qualify for this year's deduction. One thing that helped me was keeping a simple business use log from day one, even though I was using the equipment 100% for business. It's just good practice in case the IRS ever has questions. The documentation really pays off during tax season when you're filling out Form 4562. For a $5500 purchase, Section 179 can save you a significant amount compared to depreciating it over several years. Just make sure your LLC has enough taxable income this year to take full advantage of the deduction, since Section 179 can't create a business loss.

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.

As a newcomer to this community, I'm struck by the comprehensive legal concerns that have been raised throughout this discussion. The unanimous warnings from experienced members about money transmitter laws, gaming regulations, and platform policy violations paint a picture of significant regulatory risk. What's particularly alarming is the potential for retroactive enforcement - even if @KingKongZilla stops this activity now, past transactions could still trigger investigations or penalties. The IRS, state gaming commissions, and federal agencies like FinCEN don't just look at current activity when they investigate potential violations. I'd strongly recommend not just consulting with attorneys, but also proactively reviewing all past transactions to understand your potential exposure. Consider whether you need to file any retroactive reports or disclosures to get ahead of potential issues. The cost of proper legal consultation now is likely far less than the penalties and legal fees you could face if regulatory agencies discover this activity on their own. The streaming entertainment value simply isn't worth the risk of federal prosecution, substantial financial penalties, or having multiple payment processors permanently ban your accounts. There are countless successful content creators who build audiences without handling other people's money for gambling - it might be time to pivot to a completely different streaming approach.