Try and see if the following does what you want. Select events to end (right-click on the 1st event) first and then drag/drop a transition between the 1st and 2nd event on the timeline. May be even easier if you RC on the track header first and Expand track layers.

Also, if you have MSPlatinum 13, it has the Fade editing tool. You can Select events to end and Fade in all the events dragging the handle on the first event, same with Fade out. It doesn't overlap.

Using the Slideshow Creator in newer MSPlatinums helps you not forget overlapping, as you need to check the settings there.