Hi Mark,
For dotLRN you can add a batch of students to a group after they are uploaded from here.
http://gwu2.aristoi.biz:7500/dotlrn/admin/users-bulk-upload
This is not really what you want if you have many students each with thier own unique class schedules.
I started working on a data transfer project where I need to transfer grades from past classes. It uploads student_id, term_id, section_id, and grade..finds the class..adds the student to the class..then sets a grade rel.
The transcript functionality is very simple and far from finished but if it sounds usefull I can share the upload code with you and you can adapt it to your own data or use it as a model to expand user-bulk-upload to do what you need.