I’ve got a task management problem. It might be a bit different from most people’s, which may be why I’ve looked at everything from OmniFocus to Things to TaskPaper and I can’t find something that meets my needs.

What I need — and what I can’t figure out to do in any of these other applications in a reasonable fashion — is a daily log of what I’ve accomplished, from which I can cherry-pick and summarize into monthly reports, and then again into annual reports.

I can do this in my current system, which has worked pretty well for three years now. I rely on VoodooPad to keep my to-do list. Every day I assemble tomorrow’s to-do list on a page named with the next day’s date. This consists of both uncompleted items from that day’s to-do list, as well as scheduled calendar appointments.

The next day, I review and update my to-do list with calendar changes and new tasks that have come up (listed in priority order, with scheduled appointments listed above unscheduled to-dos). As I work through the day, I move items down to the ‘Done’ section at the bottom, and also add tasks I’ve performed during the day that weren’t on my to-do list at the start of the day. (Most of what I actually do wasn’t scheduled, and is heavily interrupt-driven. I need to track that work too.) At the end of the day, I copy everything above the ‘Done’ section to a new page, and begin again.

The good news is that I maintain a list of completed actions, sorted by date, and in fact chronologically within a date. These are eminently useful to me in both producing my monthly and annual “what I’ve accomplished” reports, but also as a quickly-searchable index of what I’ve done, which helps me as an information retrieval system.

For example, let’s say that someone starts asking me about Acme Widget Company. Perhaps they’ve got a new problem, or maybe they deny that we ever communicated problem resolution to them earlier. I can quickly search VoodooPad for “Acme Widget”, sort the page results by date, and see when I last talked with them. Then I can go to my e-mail, sort the correct month’s mail log by day, and find the day in question — along with an approximate time, based on the position of the item in my log in relation to scheduled events. Typically within two or three minutes I can find the precise communication referenced, and forward it to the appropriate parties.

This kind of recall makes me look like a God, an omniscient God with a long memory. And it’s something I can’t figure out how to duplicate in any of the existing task management tools.

What’s my problem, then? Three problems, one of which I believe will solve itself shortly.

The “solve itself shortly” problem is synchronization with my iPhone and iPad. But, rumor is that VoodooPad for iPad is coming, and that will help. In the meantime, I can track items on paper, or with SimpleNote, and copy those items to my to-do list manually.

The second problem is that I spend a lot of time cut-and-pasting. I could probably come up with some AppleScripts to handle the daily copies for me, but even if I do that I can’t figure out how to query Entourage so I’ll still have to add my calendar appointments manually. (I’m stuck with Entourage for the moment, due to the unbearably old version of Exchange Server we’re currently running at work. I have to coordinate with others, which unfortunately means Exchange’s calendar. If we update our server soon, I can move to iCal, but I don’t know anything that will change with regard to my core problem then.)

The third and final problem is that I’ve got no way to track events for specific future times, other than putting a calendar appointment on that date. That’s fine, if I want to allocate a specific time for something, but if I just want an item to recur on my to-do list, that’s trickier.

For example, every month I want to back up the previous month’s e-mail, so I can do my magic searching tricks. But I don’t want to put an appointment on my calendar for “the first of each month at 9 am” — after all, I might have other appointments at that time, if the first of the month is even a weekday. What I really want is, every month, the new “to-do” to show up on my to-do list as an unscheduled item. I can’t figure out how to do that using my current system.

There’s a variation on this, where I’d love to be able to note, when I send an e-mail, that I should follow up in N days if I haven’t received a response. Those, too, could be unscheduled items. But I can’t figure out how to integrate this — even as a manual note — since I’m really only maintaining one day’s list at a time.

Is there a way I can jigger my current system to give me these recurring/future-unscheduled events, and maybe reduce my cut-and-paste time as well? Is there another tool that I could switch to, which would address my issues? Or am I stuck with the shortcomings of my current system?