Trying to set up due dates for Income vs. payment schedules for repeating income vs payments due dates.
EX: Income 1 is 2nd wed of month, Income 2 is 4th Wed of month Income 3 is 1 day of month UNLESS the first is on weekend or holiday then it will be last day of month.
Can I ask whether you really want to do this type of scheduled financial planning in OmniFocus versus a dedicated financial app? You approach seems a bit misplaced relative to the strengths and weaknesses of the tools … almost like putting in a screw with a hammer.
In any case, staying in OmniFocus, are you really wanting to have incomes listed as tasks to do on a certain date? They do not seem to be “tasks to do” as opposed to “events to confirm”. An alternative in this regard is to defer them until a certain date and put a flag on them. I use this structure to pay my cell phone bill on automatic withdrawal …
Cell Phone Bill (sequential action group, flagged, repeat monthly)
get cell phone bill (deferred until mid-month after bill should arrive but before it is due, flagged)
confirm payment of cell phone bill (deferred until just after payment should be sent but just it is really due)
Finally, with regard to your specific example question …
I cannot honestly think of how to handle this convolution in OmniFocus using due or defer dates, and I am going to suggest that it is not even possible AFAIK.