Thanks everyone for the super helpful info (and video).
As usual the forum doesn't disappoint.
I checked the weep ports and see the top ones are still plugged but the bottom have had them removed. There does seem to be at least one spot where the putty sealing the window to the exterior wall of the trailer seemed to be in rough shape so I'm wondering if that's the issue.
I'll take a closer look and will likely end up pulling the window and resealing it to the trailer after we're back from our first camping trip of the season in a week and a half.
Stay tuned for more follow-up questions, I'm sure!