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I purchase the forms and software from Quill or Office Depot. It's very easy to do and you only have to issue 1099's to service workers/contractors. You don't issue them for suppliers of items (i.e., inventory, supplies). You don't have to issue to corporations however, you do have to issue to lawyers (even if a law corporation).
You mail the 1099's to each and then there is an electronic form that summarizes everything and that goes to the IRS.
I personally issue approximately 70 1099's and it takes a couple of hours to complete. Of course, that will depend on the accounting system that you use at work.
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