I have noticed this for a while, I am running Server Manager 0.9.5, so if this has been fixed, I apologize (but as far as I can tell 0.9.5 is current).
In the loadset window, if you create a folder and put transcripts in the folder that works fine. If you leave the arrow pointing down and click on a transcript below the folder (but not in the folder) and then click edit, you will edit the transcript. If you close the arrow so that it is pointing to the right and then click on a transcript below the folder but not in the folder, and click the edit button, it will open the transcript several above.
As an example:
So, the arrow is pointing to the right and the folder hierarchy is closed. I click on transcript 3 and click the edit button. Item 2 will open in the editor.