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Implement a process to have looping in the workflow without resorting to Macros. Although macros do, generally, solve the issue, I find them confusing and non-intuitive.
I would suggest looping through the use of two new tools: A StartLoop and EndLoop tool.
The start loop would have two (or more) input anchors. One anchor would be for the initial input and the other(s) for additional iterative inputs. The start loop would hold all iterative inputs until the original inputs have passed the gate and then resubmit them in order returned to the start loop.
The end loop would have three output anchors. One anchor would be for data exiting the loop upon reaching the exit condition. Another loop would be for the iterative (return) data. Note that transformations can be performed on the data BEFORE it re-enters the loop. The third would be an "overloop" exit anchor. This would be for any data that failed to meet the exit condition within the (configurable) maximum iteration expression. The data from the overloop anchor could be dealt with as required by the business rules for the unsatisfied data after being output from the EndLoop tool
The primary configurations would be on the EndLoop tool, where you would indicate the exit condition and the maximum iteration expression. The tool would also create an iteration counter field. As part of the configuration you could have a check box to "retain iteration count field on exit". If checked, the field would be maintained. If not checked, the field would be dropped for the data as it exits the loop.
This would making looping a bit more intuitive and it would be graphically self-documenting as well. Worth a mention at least.