THE 1099 MISTAKE LANDLORDS MAKE WITH CONTRACTORS AND VENDORS Every year, I send an email to more than 50,000 subscribers reminding them to collect W-9s and issue 1099s by the end of January. And every year, I get the same responses: “I didn’t know I needed a W-9,” or “My CPA never told me.” Sometimes it’s, “The contractor said his accountant handles that.” My response: “Did you pay anyone more than X dollars?” Enter the Panic Room. They all start digging through old emails, bank statements, and text messages, trying to find a tax ID for a contractor they paid months ago. Sometimes the contractor is still reachable. Sometimes they’re not. And when they’re not, what should have been a five-minute task turns into a huge headache. It isn’t really a tax problem. It’s an operating problem.
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