Great question! You're dealing with what's called "pre-rental" expenses, and the good news is that most of what you described should be deductible. Since you inherited the property in January and placed it in service in October of the same year, with clear intent to rent it out, those repair expenses should qualify for deduction. The key distinction is that repairs like fixing plumbing, patching roof leaks, and general maintenance are typically deductible in the year paid, even if done before officially renting. However, that water heater replacement would likely be considered a capital improvement that needs to be depreciated over 27.5 years (unless it qualifies for the de minimis safe harbor if under $2,500). Make sure to keep detailed records showing your rental intent from the beginning - any correspondence with contractors, rental market research, listing attempts, etc. This documentation will support your position if the IRS ever questions the timing of these deductions. Also consider whether you might qualify for Section 199A deductions on your rental income once you start receiving it - it's worth looking into for additional tax savings!

Just to add another perspective from someone who's been through multiple property acquisitions - timing documentation is absolutely crucial for pre-rental expenses. I learned this the hard way when the IRS audited one of my rental properties a few years back. Beyond what others have mentioned, I'd also suggest documenting any property inspections you had done, communications with property management companies (even if you didn't hire them), and any advertisements or listings you may have posted. The IRS wants to see a clear "business purpose" timeline. One thing that really helped me was creating a simple spreadsheet tracking all expenses by category (repairs vs. improvements) with dates and descriptions. It made tax prep so much easier and showed the IRS I was treating this as a legitimate business from day one. Also worth noting - if you did any work yourself on the property, you can't deduct your own labor, but you can deduct materials and any tools you purchased specifically for the rental property work.

This is exactly why I've been avoiding online casinos despite all the promotional offers I keep getting. The tax implications are just too messy for casual players like me who might want to try a few games with a small deposit. What strikes me most about your situation is how the current system essentially penalizes transparency. The online platforms are actually doing the "right thing" by providing detailed transaction records, but those same records end up creating a tax nightmare because every micro-transaction gets counted separately. I work in financial services and deal with tax reporting regularly, so I have some appreciation for the complexity you're facing. The fact that you need 65,000+ individual transaction records to properly report $1,500 in net winnings shows how completely divorced the tax code is from the reality of how these platforms work. Have you considered reaching out to any tax policy advocacy groups about this? Your detailed documentation of the problem could be valuable for pushing legislative reform. The absurdity of your situation - spending 50+ hours on tax prep to report a small recreational gambling profit - really highlights how broken this system is for ordinary taxpayers. I'm curious if you've calculated what your effective hourly "wage" ended up being after factoring in all the tax preparation time. Probably not very encouraging!

This is absolutely infuriating and perfectly illustrates why so many people avoid legal online gambling entirely. I'm a tax preparer who has seen this exact scenario play out for several clients, and it never gets less ridiculous. What you've described - spending 50+ hours documenting transactions to report $1,500 in actual profit while losing your standard deduction - is unfortunately completely typical. I've had clients who spent more on tax preparation fees than they actually won gambling, which is completely insane. The most maddening part is that this system actively punishes people for gambling legally and transparently. If you had just played poker with friends or bet with an offshore book, you'd have far fewer tax complications. But because you used regulated platforms that properly report transactions, you're stuck with this nightmare. I always warn new clients about this before they start gambling online, but most people don't believe how bad it is until they experience it firsthand. Your detailed breakdown should be required reading for anyone considering claiming those attractive welcome bonuses. The fact that day traders can net gains and losses while recreational gamblers can't shows how arbitrary and unfair this whole system is. We desperately need federal tax reform on gambling taxation, but until then, stories like yours serve as important warnings for other taxpayers.

I'm just starting to deal with this exact same situation with my MetLife disability payments from last year! This thread has been an absolute lifesaver - I had no idea where to even begin when I realized I never received any tax forms. The advice about checking old pay stubs first to see how premiums were paid is brilliant. I just went through mine and it looks like my disability premiums were deducted post-tax, which based on what everyone's saying here might mean the benefits aren't fully taxable. That would be such a relief! I'm definitely going to contact MetLife to get an official payment summary (and request it by email like @Harmony Love suggested to speed things up). Even if it turns out the benefits aren't taxable, it sounds like having proper documentation is crucial either way. What strikes me most about this discussion is how common this issue apparently is, yet there's so little clear guidance available elsewhere online. The combination of professional advice and real-world experiences here has been incredibly valuable. It's turned what felt like an impossible tax problem into a clear action plan. Thanks to everyone who took the time to share their knowledge and experiences - you've probably saved a lot of people from unnecessary stress and potential IRS issues down the road!

I'm currently going through this exact same situation with MetLife disability payments from my maternity leave last year, and this thread has been incredibly comprehensive and helpful! Reading through everyone's experiences has given me so much clarity on what initially seemed like an overwhelming tax issue. The key insight about checking pay stubs to determine if premiums were paid pre-tax or post-tax is something I never would have thought of on my own. I just checked mine and it appears my premiums were deducted post-tax, which could potentially make a huge difference in the taxability of the benefits. Based on all the excellent advice here, my action plan is to: 1. Contact MetLife to request an official payment summary via email (to speed up delivery) 2. Gather all my documentation including pay stubs and payment records 3. Determine the correct tax treatment based on how premiums were funded 4. Keep thorough records regardless of the outcome What really stands out to me is how proactive everyone recommends being rather than hoping the IRS doesn't notice unreported income. The stories about people getting notices years later really emphasize the importance of addressing this upfront, even without receiving proper tax forms. This discussion should honestly be required reading for anyone dealing with short-term disability payments! The combination of professional tax advice and real-world experiences has transformed what felt like an impossible situation into a manageable process with clear steps. Thank you to everyone who shared their knowledge and experiences!

Ugh, I'm in the same boat as everyone else here 😩 Filed my NYS return back in February and it's been stuck on "processing" ever since. This is my first time dealing with such a massive delay - usually get my state refund within 3-4 weeks max. The worst part is not knowing if there's actually an issue with my return or if it's just sitting in some digital pile waiting to be looked at. Really wish NYS would send automated updates or at least be more transparent about what's causing these delays. Might have to bite the bullet and try calling that support line even though 2+ hour wait times sound absolutely brutal 😤

Filed mine in March and still waiting too 😩 This thread is making me feel slightly better knowing I'm not alone, but also more worried about how widespread this delay is! The 12-16 weeks timeline @Amara mentioned is honestly terrifying - that puts me at potentially waiting until July or August. I've never had to wait more than 6 weeks for NYS before. Really considering trying that taxr.ai tool since so many people here are mentioning it. Has anyone else had success with it or found any other ways to get actual information about what's happening with their returns?

A tip from someone who messed this up last year - if you get PR packages that contain multiple items (like beauty boxes with 10+ products), document the value of each item individually rather than just the total package value. If you end up using some items for business and others personally, you'll need to know the specific values. I started taking photos of everything I receive along with screenshots of retail prices. I keep a spreadsheet with columns for: item description, date received, retail value, business use percentage, and notes about how I used it for content. My tax person said this was perfect documentation.

Great question! As someone who's been dealing with this exact situation, I can confirm what others have said - you're absolutely right that these "gifts" need to be reported as income at fair market value. One thing I'd add is to be really careful about timing. You report the income in the tax year you RECEIVED the items, not when you used them in content. So if you got that camera stabilizer in December 2024 but didn't feature it in a video until January 2025, it's still 2024 income. Also, keep detailed records of any communication with the companies. Save those emails or DMs where they ask you to feature their products - this documentation helps prove the business relationship and justifies both the income reporting and expense deduction. For your clothing example, the IRS can be picky about clothing deductions. Generally, clothes need to be unsuitable for everyday wear to qualify as a business expense. So if it's regular clothing you could wear outside of videos, you might not be able to deduct it even if you featured it in content. But specialty items like costumes or branded merchandise would likely qualify. The good news is that as a content creator, you have legitimate business expenses that can offset this additional income - equipment, software, props, etc. Just make sure everything is properly documented!