[Brian]

Okay, this may or may not be helpful, but my bank as absolutely stellar online banking; I actually just take care of all this stuff on their website, once a month. I log on, say who gets how much on what days, and they actually print and mail the checks for me and/or do the electronic funds transfer on the schedule I define.

So, rather than track each bill separately, I have a designated spot where I stick all my bills as they come in. I then ignore that spot for 27-30 days out of the month. :-)

The only thing in OmniFocus is a task that repeats 30 days after the assigned date that reminds me to grab stack 'o bills, log on to said website, and handle everything all at once.

So, if you can do the arranging that's required on the front end, you can really simplify this task down into a very small chunk of time and a single task in OmniFocus.