Just a heads up that the thresholds for 1099-K reporting changed recently, which is adding to the confusion. For tax year 2023, payment processors like Venmo only have to send 1099-Ks when payments exceed $20,000 AND 200+ transactions. For 2024 (filing in 2025), it's dropping to $5,000. The originally planned $600 threshold got delayed again. This doesn't change YOUR obligation to file 1099-NECs though. If you paid someone $600+ for services, you still need to file regardless of payment method.

I've been dealing with this exact situation for the past few years and want to add some clarity from a practical perspective. You absolutely need to file 1099-NECs for any contractor you paid $600+ during the year, regardless of using Venmo Business or any other payment processor. The key thing to understand is that YOU as the business owner have a direct business relationship with your contractors, which creates the 1099-NEC filing obligation. Here's what helped me get organized: I created a simple tracking system where I log each contractor payment as it happens, noting the date, amount, service provided, and payment method. At year-end, I total up payments by contractor to see who hits the $600 threshold. For your $14,500 in contractor payments, you'll likely need to file multiple 1099-NECs. Make sure you have current W-9 forms from all contractors before filing - you'll need their legal names, addresses, and tax ID numbers. One more tip: keep detailed records of what services each contractor provided. The IRS distinguishes between payments for services (which require 1099-NEC) versus payments for goods, rent, or other categories that might require different forms or no reporting at all.

Another often overlooked benefit is that married couples who file jointly can deduct capital losses up to $3k against ordinary income. That's $3k total for the couple, not $3k each, but still helpful. Also, remember that if one spouse doesn't work or has very low income, the working spouse can make IRA contributions for both (called a spousal IRA), effectively doubling retirement account contributions.

Great question! With your income levels ($78k and $52k), you're actually in a sweet spot where marriage will likely provide significant tax benefits rather than penalties. One major advantage not mentioned yet is the Child Tax Credit - if you plan to have kids in the future, married couples filing jointly have higher income thresholds before this credit phases out. The credit is worth up to $2,000 per child, and the refundable portion can be substantial. Also, regarding your house-buying plans, married couples get better treatment on mortgage interest deductions and can exclude up to $500,000 in capital gains when selling a primary residence (versus $250,000 for singles). Plus, if one of you has student loans, marriage might open up income-driven repayment plan options that could lower monthly payments. The "marriage penalty" mainly affects couples where both partners earn high, similar incomes (like $150k+ each). In your case, the income difference between you two actually creates a "marriage bonus" because it pulls some of the higher earner's income into lower tax brackets. You should definitely see overall tax savings!

I believe I may have some relevant insight on this particular situation. In my experience consulting with several small business clients, we've identified approximately 12-15 different IRS scam operations using similar tactics. One operation specifically targets Schedule C filers by posing as a specialized "small business division" and often uses extensions in their callback numbers. They typically reference specific deductions like vehicle depreciation or home office calculations to establish credibility. If you've shared any business information with this number, I would suggest, at minimum, filing an identity theft affidavit (Form 14039) as a precautionary measure.

Thank you all for the warnings about this scam number. I'm relatively new to dealing with IRS matters and almost called that number myself after reading the original post. It's concerning how sophisticated these scammers have become - they're clearly researching tax terminology and procedures to sound legitimate. For anyone else who might be unsure, I found that the official IRS website (irs.gov) has a "Contact Us" section that lists all legitimate phone numbers and clearly states which services require appointments or special credentials. They also have a scam reporting feature where you can submit suspicious numbers. It's frustrating that we have to be so cautious when trying to fulfill our tax obligations, but better safe than sorry when it comes to protecting our personal information.

Don't forget to call the IRS after sending important faxes to confirm they received them! I learned this the hard way when I faxed my offer in compromise docs and assumed they got them, only to find out 2 months later they had no record of receiving anything. Now I always follow up with a call about a week after sending anything critical.

Great advice from everyone here! I'd also add that if you're sending time-sensitive documents like amended returns or payment agreements, consider sending them through multiple channels (fax AND certified mail) for extra security. I've had situations where the IRS received one but not the other, and having both methods gave me backup proof of timely filing. Also, always keep your fax confirmation receipts - I scan mine and save them digitally with my tax files. The IRS can be slow to update their systems, so even if they received your fax, it might not show up in their records for several weeks when you call to check. One more tip: if you're faxing forms that require signatures, make sure your signatures are dark and clear on the scanned document. Light or blurry signatures can cause processing delays.

Don't forget you might have some interest charges even if you pay the correct amount now! Since the original deadline has passed, the IRS will likely charge interest on the $40,500 from the original due date until they receive payment.

Based on everything discussed here, I'd strongly recommend paying the amended amount ($40,500) as soon as possible and including a note with your payment referencing your amended return number. The key is getting that payment in quickly to minimize interest charges. However, given the complexity of capital loss calculations that others have mentioned, I'd also suggest having a tax professional review your amendment before you submit it. With amounts this large, the cost of a professional review is worth avoiding potential errors that could trigger an audit or result in owing even more. If you need to speak with the IRS directly about your specific situation, it sounds like services like Claimyr can actually get you connected to a real agent, which might be worth considering given how difficult it normally is to reach them. Getting confirmation directly from the IRS about how to handle your payment could give you peace of mind.