Hi Christina,
You could use the rule based on the user's first login date, but that presupposes they're going to login whenever they start (or near that time).
You can set the rule 'before previous X days' or 'within previous X days'.
Also there's a job assignment relative date rule you could use.
Or you could use a course completion rule where the course stands for some kind of registration process.
let me know what you think,
cheers,
George.