What is the duration of your video transition...the default 1 second or less or other?
What are you using - Cross Dissolve and specifically named, what else?
Of the video transition alignments (Left Clip, Between Clips, Right Clip), you have apparently tried Between Clips and Right Clip.
Did you try Left Clip? That seems to work for me in the interesting situation that you present.
I just settled on a 2 second dip to black, between clips, which fades out my video clip and doesn't extend the play beyond the trimmed part. Now I can't duplicate the problem I had. Maybe rendering or saving the project "fixed" things.
Thanks for the follow up.
I was able to replicate the original issue that you described, using my Premiere Elements Windows. So, what you reported was not just a Premiere Elements Mac Windows one time happening. But, the issue was addressable with alterations in the video transition properties/settings of a particular video transition and trim considerations for the video still files involved.