It’s somewhat laughable that in 2010, Outlook still lacks the basic software intelligence to help make the lives of its users easier. If there are known elements (day of the week, day of the month, a time, and a time zone) it shouldn’t be difficult to create a function in the software that would automatically parse and order that data into an appointment – all that would be missing is a description and location (though the latter could be part of the data points). Despite everyone embracing the cloud, I still stand by Outlook as my pain productivity weapon for email, calender, tasks, contacts, etc. It works extremely well for me – far better than any cloud-based solution I’ve tried.
I should add that I’ve seen some Outlook add-ins that do some things like this – specifically with contacts – but I don’t like loading up Outlook with add-ins. The core functionality of Outlook needs to improve.