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Any progress on this?
I have to admit we haven't made the time to get to your enhancement request for CheckBook's Schedule Entries. I can say that we're wrapping up 2006 business this week and will be almost exclusively about CheckBook 2.0 through 2.1 for the foreseeable future. We will try to get things working as you'd like in 2.0 but it may have to wait until a minor release on the way to 2.1.
Just to be sure we're on the same page, your Schedules need to repeat on specific instances (1st through 4th, or last) of specific days of the week in specific months, right? For example, the 2nd Friday of every month or the last Monday of February, similar to what can be set up with iCal's custom repeat options. What if we extend the "Repeat Every" part of the Schedule interface to include these kinds of options? CheckBook should already work well for the rest of the examples you gave from Now Up-to-Date. Repeating a specific number of times is also already part of CheckBook.
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Let's compromise: Just add a button on the SCHEDULE page next to each item that says: "APPLY NOW" and we could live with that for a while by doing it manually. We don't even have that option as it now stands.
The Look Ahead feature we introduced earlier this year should help with this, allowing you to see the Scheduled Entries that will become due a specific amount of time into the future and commit them in advance.
We've always had it in mind to add a contextual menu item to each Schedule so the user can commit the next due Scheduled Entry. Would that work for you?
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Could there be an option to automatically apply scheduled entries please?
We're extremely reluctant to provide this option because we're concerned about how it would affect less experienced users.
Committing automatically would really hurt if a user mistyped the Start Date for a Schedule, such as entering a year at some point in the past. That would bring a wave of unwelcome Scheduled Entries into the current Account. This could also happen if the date on the Mac is just plain wrong and happens to be wrong into the future rather than the past. With the Schedule Reminder we're trying to give users a sporting chance of seeing the trouble before it comes to pass. The Schedule Reminder also gives users a way to try various Schedule options to see how they will play out without actually affecting their Accounts.
If we do provide an option to automatically commit it would have to come with a very strong warning about the very painful possibilities. Even then I suspect some less experienced users would skip the warning text. It might be better as a hidden preference, only available to users familiar with the defaults command-line tool or editing user defaults property lists by hand.