1099-Misc Questions, Difficulties & Musings

[Luke Stone]

I have a couple questions, but I guess this is as much a venting post too

Questions:

1) The W9 form has check boxes for C Corp and S Corp. Since we don't need to fill 1099-Misc for corporations do we not file it if one of these boxes is checked?

2) Single member LLC's don't have to have 1099-misc filed either, but multi member LLC's do. How do we figure this out? Just ask? My conversations with contractors don't generally include discussions about their business entity structure...

3) If I do accidentally file a 1099-misc on a single member LLC or corporation, does it penalize them/are being taxed double for income they only collected once?

The venting...

I feel this is a very poor way for the government to implement income for the gig/small business economy. The sharing economy is a rapidly growing part of the economy and this brings a unnecessary and a significant degree of complexity. Basically any small business now has to be a semi CPA. 

Another issue there are a lot of unscrupulous people in the small biz/underground economy world and if I were a contractor I would not feel comfortable giving out my social security number.

Don't get me wrong I understand why these rules were put in place and there is a huge underground economy that is not paying taxes. Just seems this method creates more trouble than it's worth....

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