LOL, yeah, that's probably me. I just picked it up from Stivers on Tuesday. I've only seen one other 2011 Explorer, Bordeaux Red with Gabus plates, I assumed it was just a test drive. I'm sure there is more as a Stivers salesman bought one for his wife, not sure what color that is.
I know the sensation you're referring to as I've experienced it in all my manual vehicles in the past when I shift to high at low speed. It does sound like your transmission is confused as to when to shift and I usually see this at a normal cruising speed where you let off the gas at X mph and then just rest your foot on the pedal. It could be the tranny learning your driving style as you mentioned. What happens you when you really step into it just as it bogs down? Does it drop down a gear (like you are getting on the interstate for example)?