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Old 05-24-2022, 08:25 PM
BobC BobC is offline
Bob C.
 
Join Date: Apr 2009
Location: Ohio
Posts: 3,276
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Quote:
Originally Posted by Exhibitman View Post
I really think people are overthinking this. If I am selling an investment and I have documented the cost basis for the item and the net I receive from the sale, characterizing it is my choice on my tax return (investment or business). As long as I accurately report my profit, in whatever form, there should be no problem in the end. I get a 1099 from Vanguard and Schwab for my investment income. That doesn't mean I am a stock brokerage, even if I trade every damn day.

Now, I could see the states getting pissed if there was no sales tax remittance from frequent selling 'investors', but eBay collects the sales tax for the sellers, so that isn't an issue either.

I just don't see how a 1099 in and of itself makes you run away from the platform unless you are a tax scofflaw.

And don't think for a minute that this won't eventually get to auction houses. The big internet selling platforms were the first, but a multi-billion-dollar business is certainly going to attract the attention of the revenue agencies.

if you want to cheat the tax man, you have to go with cash and that cash can never, ever formally enter the financial system. And that is when you visit the cross-bar hotel if you get caught. Just pay your taxes. It's easier.
Adam,

I'm not talking solely about just tax cheats, and yes, there are those. There are also people who are deathly afraid of sharing anything with the IRS, and it isn't always because they are tax cheats and/or not paying their taxes. You should see what happens on occasion when asking someone if they want their tax refund check direct deposited into their bank account, rather than having to wait for a paper check in the mail, and the possibility of it being lost, stolen, or whatever. Suddenly having another piece of paper regarding some aspect of their life and/or business now going into the hands of another government agency does not sit well for many more people than you may realize. I have come to respect such people's sentiments over the years and not be quick to judge them. You should try doing the same!

Go talk to your Uncle if you can. Maybe he can better explain the potential nuances to you. Of course, being a tax attorney, as you said he was, doesn't necessarily mean he was always doing personal tax returns for individuals and small businesses, and therefore was maybe talking to you in more general terms and not about specific instances or circumstances that are definite grey areas of the tax law, and subject to different interpretations and treatments. I don't know his exact background and experience, so I can't speak to that.

I obviously know that tax evasion is a crime, but I also know for a fact that tax avoidance is your constitutional (and God given) right! LOL And pretty much all of the tax related comments and statements I make are to point out the potential differences and nuances (and grey areas) that do exist in the tax laws, and to hopefully show other members on this forum many of those potential legal differences and interpretations for which a taxpayer may have to make choices, based on each one's unique set of facts and circumstances. You seem to have your own personal tax situation figured out and settled as to how you want things handled to your satisfaction, which I think is absolutely fantastic. But please remember that what may make sense and be right for you, isn't necessarily always the best, most accurate choice, for others. Have a great evening.
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