When using the Square reader, is it considered taxable income? I don't meet Square's requirements for the 1099-k so it's a bit of a grey area for me. I just need to know if I need to prepare to make a payment to the IRS for these transactions?!
If the money you receive via Square is taxable income, then the IRS will want you to report it regardless of whether you get a 1099-K from Square.
Just because you receive the money via Square doesn't make it taxable -- if a friend borrows $100 from you and pays you back via Square, that's not taxable income. If you sell jewelry for $100 to someone, and they give you the money for it via Square or a check, then it is taxable income.