Different software needed for elearning

I am just completing an associates in Web Design and Interactive Media so I am still very new to all this.  I am trying to learning everything I can get my hands on.  I am hoping for a little guidance on what software is best for my longterm goal.  What I plan to do is create a site that is elearning and would not only keep track of the scores of the student, but to determine which lessons to send the student to next depending on the score they received.  I want to be able to customize the look so it isn't the same as everyone else that uses the same software.  I also want things to be random.  For example, different questions each time instead of each student receiving the same questions on each quiz.  Different subjects can be  chosen at different times by the student as well and the classes are done completely at their own pace.  A timer would also be included for a "recess" from the lessons.

I initially planned on just using flash but I am not sure about it keeping track of the scores and adjusting the lessons accordingly and also would prefer for the site to be able to be accessed for ipads etc that don't have flash.  Ideas?  Thanks.