@RectorSeal_Jason there are a couple of areas I would look.
First, in your iterative macro you should have two separate sections. The first being what comes out of your iterative macro when it matches the iteration number. The second section should be what does not match your iteration number and is then looped back. In that second section, the data in the macro output *needs* to have the same/identical fields as the data set that came in to the macro to begin with. If it doesn't, you'll see that "Iteration #2: Tool #4: The field "Date" is missing. Compare the tool configuration with the input stream" error you are seeing. On that second iteration, the macro is looking for the Date field. Somewhere in your macro, that Date field was dropped.
For the "Iteration #2: Tool #25: The field schema for the output "loop" changed between iterations." error:
This typically happens when the output changed schema. That is, the number or data types of the fields changed between different runs. For example, if the data originally came in as a Double field and then changed to V_W String somewhere in the macro, you'll hit that error. Another reason for it comes from when your Interface Designer - Property settings are set up so that "All iterations will have the same output schema (Error if different)". Unsure how the macro is established, but I would check in to "Auto Configure by Name" or "Auto Configure by Position". In both settings, all iterations will run before Alteryx decides how to display the data from the macro's output.
Double check the Select tool that is feeding the Macro Output tool. Make sure each field matches (e.g. data type, data field name, etc.).
