insufficiant content for edit
 

how do I add transitions to clips that are between 10-20 seconds in length w/o getting this "insufficiant content for edit" crap? anybody run into this thorn before?

Think about it: If you are doing a transition, you need footage from both of the clips. If there is not enough footage for the transition, you cannot do it.

One way to put the transition in is to get rid of a bit of each clip, move them together, then drag the transition on. You need "hidden" footage there for the transition to work.