THE LANDLORDS WHO BREEZE THROUGH JANUARY DON’T HAVE MAGIC TAX SKILLS. THEY JUST HAVE A SYSTEM.
GET THE W-9 BEFORE YOU PAY You should not wait until December. Getting the W-9 upfront reduces last-minute stress. Because that’s when it’s actually easy to get. After the payment is gone, you’re just chasing. I am guilty as charged as well. Last year, a tenant called at 5 am, panicking that the water heater burst. The foyer area flooded, and the flooring warped. I find a contractor who can get there in 20 minutes. I’m not thinking about W-9s. I’m thinking, stop the water.
He fixed the leak and I paid him the next day, thinking I’ll get the W-9 later. But the problem started later. Luckily, he did send me the form on January 29th after 20 reminders. Last month, I was talking to an investor running a seven-figure portfolio. He didn’t even know he was exposed on 1099 compliance. When I asked him about it, he just said, “Nobody ever told me.” That stuck with me.
BECAUSE THAT’S THE REAL PROBLEM. EVERYONE ASSUMES SOMEONE ELSE IS HANDLING IT.
• The contractor thinks you’ll ask for a W-9. • You think the bookkeeper has it.
still owes you money. But once you scale, that stops working. More units = more vendors. More vendors = more invoices. More invoices = more chances to say, “I’ll get that later.” The landlords who breeze through January don’t have magic tax skills. They just have a system. And the best system is the simplest one:
• The bookkeeper thinks the property manager got it. • And the tax preparer thinks everyone did their job.
When you have one or two properties, you can run everything in your head. You remember who did the plumbing, who painted the unit, and who
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