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You should think more about standardizing your own workflows and habits. Its more about you than the software in this case, i.m.o.

I don't think pushing due dates is a good idea at all. Set a due date and let it be hard. Then put a next review of e.g. 1 day. Now, if you make certain that you review every day; that project will be popping up every day and you can decide on a daily basis if you want to contact that guy and ask him how that task is moving. Use flags if you want, it doesn't matter (although flags can be used for individual actions). Again you must make absolutely sure you review all flagged items daily. Its about getting into a routine...