Learning any software package in a vacuum -- by yourself -- is not fun. You may become functional in the software, but those tricks that will make your life easier are learned by interacting with other people. This is true for digital asset management software.
Have you connected with other users? Do you know who they are? Have you asked them questions? Have you looked over each others' shoulders? If you haven't, check with the sales staff for your software and see if they can put you in touch with other users in your region. Better yet, ask if there is a user group meeting.
Speaking of the need to lean on others...
CONTENTdm seems to be one piece of software that truly requires interacting with others in order to learn. While there are extensive help pages and support from OCLC, the trick seems to be interacting with other users during the learning process. One person said that there are feature that you rarely use, so it's best to find someone to walk you through them rather than struggling on your one. In the U.S., regional CONTENTdm user groups have sprung up. For example, the Eastern CONTENTdm Users Group will have its third annual conference this summer at West Point.