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I'm one of the people you're talking about. I tried it and it had the opposite effect. I tried to do it with the plain forms once about 15 years ago. Somehow

I'm one of the people you're talking about. I tried it and it had the opposite effect. I tried to do it with the plain forms once about 15 years ago. Somehow I ended up reporting the same input twice or something? I'm still not sure what I did wrong, but I ended up getting taxed for income that didn't exist. I didn't know how to correct it. I wrote letters and called the IRS probably dozens of times. I spent more than 50 hours poring through documents trying to figure it out. I tried to find an accountant that could understand what was happening. Eventually, it went away. I'm not sure what I did differently or if the IRS just got tired of dealing with me and waived it. I was probably doing all of this incompetently, but I could not get a "foothold". I have somewhat of a tax phobia to this day. The problem had something to do with some independent contracting I had done that year. I just resolved not to do that anymore.

dmoy 3y ago
Shoot, I accidentally reported the same income twice even with turbotax once because I didn't understand what non-covered shares were. (And in my defense, the broker also didn't show cost basis on the 1099-B either, I was just supposed to know)
- ghaff 3y ago
  I forget when the cost basis reporting requirements got firmed up but there were some point where I had options from a former employer that had gone through a couple rounds of acquisitions and when I eventually sold the shares I ended up throwing my hands up a plugged in some average cost basis that was somewhere in the ballpark and called it a day. It's all pretty automatic these days but it used to often be a real mess to try to do accurately.
  - dmoy 3y ago
    Yea cost basis reporting from the broker to you is better now. Cost basis reporting from the broker to the IRS is still blank for non-covered shares though, which leads to the other common case of "forgot a page of 1099, IRS thinks it's $0 cost basis, sends bill for $10k++, but actually you owe ~$0 if you send in the correct info".

dmoy 3y ago

Shoot, I accidentally reported the same income twice even with turbotax once because I didn't understand what non-covered shares were. (And in my defense, the broker also didn't show cost basis on the 1099-B either, I was just supposed to know)

ghaff 3y ago
I forget when the cost basis reporting requirements got firmed up but there were some point where I had options from a former employer that had gone through a couple rounds of acquisitions and when I eventually sold the shares I ended up throwing my hands up a plugged in some average cost basis that was somewhere in the ballpark and called it a day. It's all pretty automatic these days but it used to often be a real mess to try to do accurately.
- dmoy 3y ago
  Yea cost basis reporting from the broker to you is better now. Cost basis reporting from the broker to the IRS is still blank for non-covered shares though, which leads to the other common case of "forgot a page of 1099, IRS thinks it's $0 cost basis, sends bill for $10k++, but actually you owe ~$0 if you send in the correct info".