Transfer Applications: Keep it to one, or try try try every time?

If a student wants to transfer to a different college with multiple transfer application options available (Fall 2nd year, spring 2nd year, fall 3rd year, spring 3rd year) during their time in their original college, is it better for the student to apply one time or for the student to apply all four times, each successive time with an improved application?

I can think of reasons why both would be good ideas if a student really is determined to transfer into that college. What do some of you think, whether you be students or parents or counselors or admissions folk?

Note: Pretend money, time, and effort are no object.