The built-in TimeOfXXX timers in Lookout should do the job. These timers basically let you configure them in a way that they fire every minute, hour, day, week, month, year at a pre-defined point of time. And for Holidays, the "Today" function might be helpful. See Online Help for full details on all these.
The above should take care of most of your tasks. However, for the odd ones, you can always use Microsoft's Calendar Control as an ActiveX Control in Lookout.
Hope this gives you some ideas.
Disclaimer: the above are general suggestions -- NOT promises NOR guarantees. Please don't take my word as-is; make sure Lookout does indeed lends itself to all your needs beforehand. I don't like no lawsuits maan 😉
Regards,
Khalid
