Hi Scotty- hope you are well.... I am having same problem as a few months ago....some calendar items are automatically syncing to iphone, others are not....can't figure out why some are/are not.  I have gone in to manually sync and checked mobile me info...all looks fine...any suggestions?
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The most likely cause is that you have accidentally created two families of calendars and are adding events to the wrong calendar. The first family of calendars should be under “MobileMe”. These calendars should be syncing however the second family may be called “on my mac”. If you have any of these calendars listed then most likely those are the problem. In 10.6 you should see your calendars on the left hand side of iCal. In 10.7 you need to click the “calendars” button in the top left hand corner of iCal and it will list the calendars as a drop down menu. Subsequently you should check on your iPad or iPhone under calendars in the calendar program to see if there are multiple families of calendars there as well. You may also want to look in the settings apps on your iOS device and go to mail, contacts, and calendars. Scroll all the way to the bottom and check to see what calendar is your default calendar.

If this is true and you’ve accidentally created a “on my mac” calendar (taking for granted that you were using MobileMe) then we’ll need to re-migrate those calendars back to the MobileMe calendar family. Hope this makes a little sense.