I'd strongly recommend consulting with a tax professional about your specific situation. While the advice here is generally solid, there are some nuances with owner-occupied rental properties that can get complex. For instance, you mentioned your mortgage interest was $12,400 - you'll need to split this between your personal residence portion and the rental portion. If 30% of your home is rented out, then 30% of that mortgage interest ($3,720) would go on Schedule E as a rental expense, while the remaining 70% ($8,680) can still be claimed as an itemized deduction on Schedule A. Also, be very careful about the depreciation deduction that was mentioned. While you can depreciate the rental portion of your home, there's a "recapture" rule that means you'll have to pay back some of that depreciation benefit when you eventually sell the house, even if it's your primary residence. This can be a significant tax hit later. The bottom line is that yes, you absolutely need to report this income - but with proper planning and documentation, the tax impact may be much less than you think. A good tax preparer can help you navigate these rules correctly and make sure you're taking advantage of all legitimate deductions while staying compliant.

I understand the temptation to not report it since it's through Venmo, but you really need to report this rental income. The $27k you collected is significant income that the IRS expects to see on your return. Here's what you should know: You'll report this on Schedule E (Rental Income), but the good news is you can offset a lot of it with deductions. Since you're renting out rooms in your primary residence, you can deduct the rental percentage of expenses like mortgage interest, property taxes, insurance, utilities, repairs, and even depreciation. For example, if the rented rooms represent 25% of your home's square footage, you can deduct 25% of your qualifying home expenses against that rental income. With your $12,400 in mortgage interest alone, that could be around $3,100 in deductions right there. Don't risk tax evasion charges over this - the penalties and interest aren't worth it, especially when proper reporting with deductions will likely result in much less tax than the 25% you're estimating. The IRS has been cracking down on unreported income, and payment apps are reporting more transactions than ever before. I'd strongly suggest getting help from a tax professional for your first year doing this to make sure you capture all the deductions you're entitled to and set up good record-keeping practices going forward.

This entire discussion has been incredibly enlightening! As someone who's been lurking on tax forums trying to figure out my own social casino situation, this thread answered questions I didn't even know I should be asking. The methodical approach everyone has outlined is spot-on: get those detailed CSV transaction histories from the platforms, calculate your actual net gambling losses, then run the math on itemized vs standard deductions. What really impressed me is how several people achieved substantial tax savings ($1,400-$2,800) by taking the time to properly document their losses instead of just paying taxes on gross withdrawals. The documentation requirements seem much more manageable than I initially thought. Having the platforms provide comprehensive CSV files changes everything - it transforms what could be a nightmare of reconstructing records into a straightforward process of organizing existing data. For your specific situation with $33k in withdrawals, definitely start by contacting Modo and Crown Coins customer service for those complete transaction histories. If you deposited more than you withdrew (which sounds likely based on your comments about overall losses), those gambling losses combined with your other itemized deductions could result in significant tax savings. Either way, you're being smart to think this through carefully rather than just guessing at the best approach. Thanks to everyone who shared their real experiences - this kind of practical guidance from people who've actually navigated these issues is invaluable!

This has been such a thorough and helpful discussion! As someone who's dealt with social casino taxes myself, I can confirm that the systematic approach everyone has outlined really works. One additional tip that helped me: when you request those CSV transaction histories from Modo and Crown Coins, also ask if they can provide any year-end summary statements. Some platforms offer these and they can be helpful as supporting documentation alongside the detailed CSV files. Also, don't forget to factor in any promotional credits or bonuses you received when calculating your actual deposits. These count as part of your gambling activity for tax purposes, so make sure they're included in your loss calculations. Given your $33k in withdrawals and the fact that you mentioned losing more than you won overall, there's a good chance your gambling losses could be substantial enough to make itemizing worthwhile. The key is getting those detailed platform records first so you can calculate the actual numbers rather than estimating. The documentation approach that's been discussed here (platform CSV files + bank statements + withdrawal confirmations) should give you solid records regardless of which deduction method you ultimately choose. Just make sure to keep everything organized - good record-keeping protects you whether you itemize or take the standard deduction.

Has anyone used QuickBooks to generate their 1099-NECs for medical contractors? I'm trying to figure out if it correctly handles the different boxes for 1099-MISC vs. 1099-NEC and I'm getting confused.

As someone who's dealt with similar contractor classification issues in healthcare, I'd strongly recommend double-checking whether all your medical professionals should actually be classified as contractors versus employees. The IRS has gotten much stricter about this, especially in healthcare where there's often significant control over how and when services are provided. For hospice care specifically, if you're setting schedules for on-call physicians, providing equipment, or directing how they provide care to patients, you might need to reclassify some as employees rather than contractors. This would mean W-2s instead of any 1099 form. The control test is really important here. That said, for legitimate contractors, you're right that 1099-NEC is typically the correct form for professional services. Just make sure you can pass the IRS contractor test first - it'll save you major headaches down the road if they audit your worker classifications.

Thank you all for sharing such detailed experiences - this thread has been incredibly informative. I'm in a similar situation where I have evidence of significant tax violations by my former employer, and reading everyone's real-world experiences has been much more helpful than just looking at the official IRS guidance. A few additional questions that haven't been fully covered: Has anyone here dealt with a situation where the company might have already corrected some of their violations after you left? I'm wondering if the IRS still pursues cases where partial corrections have been made, or if they only focus on ongoing violations. Also, for those who mentioned the emotional toll - did any of you experience anxiety about potential retaliation even before submitting? I've been hesitant to move forward partly because I'm worried about my former employer somehow finding out I'm even considering this, even though I haven't submitted anything yet. The information about calling the Whistleblower Office directly at 202-622-7104 is really valuable. I think I'll start there to get clarity on some of the technical aspects before deciding whether to proceed. The stories about successful awards, even with long wait times, are encouraging that the system does work for legitimate cases with good documentation.

This has been such a helpful thread - thank you everyone for sharing your real experiences. I'm actually in a very similar situation to the original poster, having left a company where I witnessed systematic tax fraud involving fabricated expenses and hidden revenue streams. One thing I'd like to add based on my research is about the statute of limitations. The IRS generally has 3 years to audit tax returns, but this extends to 6 years if there's a substantial understatement of income (25% or more). For cases involving fraud, there's no statute of limitations at all. So even if some time has passed since you witnessed the violations, it may still be worth reporting. I've been hesitant to move forward because I'm worried about the time commitment and emotional energy required, but reading about people who have successfully navigated this process - even with the long wait times - is really encouraging. The point about civic responsibility really resonates with me too. These companies are essentially stealing from all taxpayers when they avoid their obligations. Has anyone here had experience with cases involving international transactions or offshore accounts? My former employer had some suspicious dealings with foreign subsidiaries that I suspect were being used to shift income overseas. I'm wondering if these types of cases get handled differently or require additional documentation.

Someone mentioned PFIC earlier and that's actually super important. If your foreign ETFs are considered PFICs (most are), you might need to file Form 8621 for each one, even if they're held in a US brokerage!!! That's separate from the 8938 question.

Thank you all for this incredibly helpful discussion! As someone who's been dealing with similar confusion, I wanted to add a few clarifications that might help others: 1. **Form 8938 vs FBAR**: Both commenters above are correct - since your Chase account is with a US institution, you don't need either form, regardless of what foreign investments are inside it. 2. **PFIC trap**: @Yara Assad and @Olivia Clark are absolutely right about this being a separate issue. Many foreign ETFs are indeed PFICs, and Form 8621 requirements apply regardless of where the account is held. This is often overlooked and can result in significant penalties. 3. **Common mistake**: I see people get confused because they think "foreign investment" = "foreign account" but the IRS distinguishes between the location of the financial institution vs. the underlying investments. @Tyrone Johnson - for your specific situation, I'd recommend asking your accountant to specifically verify whether any of those foreign ETFs qualify as PFICs. The portfolio manager at Chase should be able to provide you with a list of all foreign funds purchased during the year so you can check each one. The tax software and IRS callback services mentioned above sound like great resources for getting definitive answers on these complex international tax situations.