#1: You need to illustrate with screen shots. And are you aware that regular custom fields are not the same as line-item custom fields? The dropdown list feature has not yet been implemented on line-item custom fields. See this topic: Problem with drop down list option in line custom fields.
#2: No one and no Guide ever said a date picker would be available for custom fields. Selecting Date as the field type for a custom field only means the program will treat the field as a date instead of a text string.
#3: First, Manager is not a what-you-see-is-what-you-get program. Second, what type of field did you choose? And what size?