This is my first year using Square for our 1099 filings for contractors and it has been a mess to say the least. I want to request one (relatively simple) feature that would save a huge amount of time. The ability to designate contractor payments as reimbursements so that they are not included in the 1099 total at the end of the year.
Hey there @C1VB. This is definitely something that I think Square should look into. This Community has what is called the Ideate Board, where we can formally submit feature requests for evaluation and a decision about whether or not the team wants to add a feature to the product roadmap in the future. You should go there and copy/paste your post above into such a request. When you do, please come back here and post a link to that request. Will definitely give it my support, and other sellers probably will, also.
For now, though, all I could recommend is that you refrain from paying reimbursements through Square. In my shop, for the few rare occurrences we have for this, we just book it in our accounting system and pay it by either check or card. That way, we can book the expense properly and prove that this IS actually a reimbursement per IRS rules.
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