Hey Hugh! I totally get your confusion - I was in the exact same situation when I started my first job after college. The terminology on those HR forms can be really intimidating! For most U.S. citizens like yourself, your TIN (taxpayer identification number) is simply your Social Security Number (SSN). They're the same thing! When the forms ask for your TIN, just enter your 9-digit SSN. You can find your SSN on your Social Security card, any previous tax documents if you've filed before, or even on bank statements or other official paperwork where it appears. The reason this seems confusing is that "TIN" is actually an umbrella term that covers different types of tax identification numbers: - SSN for individual U.S. citizens (which is what you'll use) - EIN for businesses - ITIN for certain non-citizens who need to file taxes But for regular employment paperwork as a U.S. citizen, your SSN serves as your TIN. You don't need to apply for anything separate - just use the Social Security Number you already have! Don't stress about it - the forms make it sound way more complicated than it actually is. You're doing fine, and using your SSN when they ask for a TIN is exactly what you're supposed to do.

Hey Hugh! I totally understand the confusion - this tripped me up when I first started working too. For most U.S. citizens like yourself, your TIN (taxpayer identification number) is exactly the same as your Social Security Number (SSN). When your HR department asks for your TIN on those forms, just enter your 9-digit SSN. You can find it on your Social Security card, previous tax returns if you've filed any, or other official documents like bank statements. The confusion comes from the fact that TIN is actually an umbrella term covering different types of tax ID numbers - SSNs for individuals, EINs for businesses, ITINs for certain non-citizens, etc. But for regular employment paperwork as a U.S. citizen, your SSN is your TIN. Don't worry about putting the wrong information - you're doing exactly what you're supposed to do by using your SSN when they ask for a TIN. The forms make it sound more complicated than it really is!

Another option is to request a "Tax Return Transcript" from the IRS, which is different from the Account Transcript someone mentioned above. A Tax Return Transcript will only be available for years you actually filed a return. So if you request one for 2019 and they say no transcript is available, that's a pretty clear sign you didn't file for that year.

Just wanted to share my experience with a similar situation. I had unfiled returns from 2018 and 2019 that I wasn't sure about, and like you, my IRS online account showed zero balance. I ended up using a combination of the approaches mentioned here. First, I requested Tax Return Transcripts for both years through the IRS website. For 2018, no transcript was available (meaning I hadn't filed), but for 2019, there was a transcript showing I had filed but with incorrect information. This gave me a clear picture of what I needed to fix. The key thing I learned is that zero balance doesn't mean you're fully compliant - it just means you don't owe money right now. The IRS can still come after you for unfiled returns even if you don't owe anything, and there can be penalties for late filing regardless of whether you owe taxes. Since you already mailed in your 2019 W2, I'd recommend requesting that Tax Return Transcript for 2019 in a few weeks to see if the IRS processes it and updates your filing status. That way you'll know for sure if everything is squared away.

Just a heads up - make sure you're tracking the "unadjusted basis" correctly. This should be the original cost of the building portion only (not including land) before any depreciation. For an inherited property, it would typically be the fair market value of the building (not including land) at the time of inheritance. So if your property is worth $320k total but $50k of that is land value, your building basis would be $270k, making the 2% threshold $5,400. That would be lower than the $10k cap, so $5,400 would be your safe harbor limit.

This is such a helpful thread! I'm dealing with a similar situation with my rental property. One thing I want to add is that documentation becomes really important when you're near or over the safe harbor limits. I learned this the hard way during an audit a few years ago - the IRS agent wanted detailed records showing exactly what work was done and why it was necessary. For repairs like your HVAC replacement, having documentation that the old system was broken/non-functional (like repair estimates or photos) really helps support the "repair" classification versus "improvement." Also, timing can matter. If you're close to your safe harbor limit and have discretionary maintenance work planned, you might consider spreading it across tax years to stay under the threshold when possible. Obviously you can't delay emergency repairs like your mold situation, but things like painting or minor updates could potentially be timed strategically. The inherited property basis calculation mentioned above is spot on - make sure you're using the stepped-up basis correctly and allocating between land and building properly. A good appraisal from the time of inheritance can be invaluable for this.

I'm in my 3rd year of YouTube and my biggest mistake was mixing personal and business expenses at the beginning. For your sanity during tax season, get a separate card for YouTube purchases NOW, even if you're not making money yet. When tax time comes and you're trying to sort through hundreds of transactions to figure out which were for the channel... it's a nightmare. Trust me.

Great thread! As someone who's been through this exact journey, I want to emphasize something that saved me a lot of headaches: start treating it like a business from day one, even if you're not making money yet. Beyond what others have mentioned, here's what I wish I'd known: consider opening a business credit card (not just debit) for your YouTube expenses. Many business cards offer cash back on categories like office supplies, internet, and advertising - which are perfect for YouTubers. Plus, using credit responsibly helps build your business credit score for the future. Also, don't forget about the home office deduction if you're editing at home! Even if it's just a corner of your bedroom where you edit, you can potentially deduct that square footage. For 2025, you can use either the simplified method ($5 per square foot up to 300 sq ft) or calculate actual expenses. One last tip: start a simple spreadsheet or use an app to track everything monthly rather than waiting until tax season. I use a basic Google Sheet with columns for date, amount, category, and description. Takes 5 minutes a month but saves hours at tax time!

Has anybody used TurboTax Self-Employed to handle amortization of business acquisitions like this? I'm wondering if I need to pay for a CPA or if the software can handle it properly.

I went through something very similar when I purchased a small accounting practice last year. One thing I learned that might help you - make sure you're crystal clear about whether any part of your $27k included a non-compete agreement with the previous owner. Even if it wasn't explicitly called out in your contract, if there was any understanding that the seller wouldn't compete with you for a certain period, that portion needs to be amortized differently. Also, don't forget to consider if any of the customer contracts you acquired have specific terms or remaining durations. Sometimes part of the purchase price can be allocated to these existing contracts, which might have different tax treatment than pure goodwill. Your tax professional will definitely help sort this out, but having these details ready will make that meeting much more productive. Good luck with the expanded business!