I do some similar things. I use the recurring feature with Outlook to set items which occur at specific intervals (monthly, weekly, even yearly). In combination with this, I also use my tickler system if I have something that is paper-based and would be easier simply to drop into a folder. If it is recurring, I either move it to the next date when I come to on a specific date, or I might make the note on separate pieces of paper and drop them in the specific dates for the whole year.
I've also found I can put some of these types things on my calender (day specific or time specific). I've found this works best for keeping track of birthdays and anniversaries.
The only caution I'd offer is something I've noticed with my system. I have to be careful that I don't have too many things that are popping up all over my computer screen which aren't crucial matters for me to deal with. I tend to go numb to them if I have too many popping all the time. So, by splitting the things across platforms (Outlook recurring, tickler system, calender), it tends to help me stay engaged with them.