If I have Status A and I want Transition in between Status A and Status B, why can't I have more than one transition between those to Statuses? 

What I want is to have different conditions in each of the transitions. If specific criteria is met for 1st Transition, it will go through that and I will have actions "During" that transition. If the criteria on the ticket is met for it to go through the 2nd Transition, then I will have different set up things that will happen "During" that transition. Maybe I'm missing something obvious. I'm new to Blueprints, but when I tried it wouldn't let me set up more than one transition between two statuses.