Insist on a sterile environment while doing your "preflight" walkaround. That's what pilots do, and it works. No chitter chat or doing things out of sequence. If two people are performing the checks, one needs to be responsible for each task, otherwise you can end up with the "I thought you were checking that" scenario. 

In pilot training I got that drilled into me, my flight instructor would deliberately try to distract me and then point out anything I missed because of the distraction. Annoying but that's how you learn. 

I have no problem stepping over the tongue or opening the tailgate while hitched. The Hensley Cub hitch is different in that the major part of the hitch stays permanently attached to the tongue and only a bar is placed into the receiver (straight or offset). Then the bar is backed into the hitch opening and locked into place with two locking arms. This actually sets the tongue back farther than a straight WD hitch with bars like our former Equal-i-zer or an E2 hitch would, giving plenty of room. Also, the way the Hensley Cub is articulated, we can make some pretty sharp turns, either forward or backing.

As for a Jack-E-Up, it would not have helped where I forgot to retract it in the first place. Also, I don't see this working with a flip-foot mounted as the flip-foot would need to be removed each time before the jack is removed, which would be a non-starter.

Let your hands touch the items as you move along, this creates a physical memory. And, never allow yourself to be distracted while doing your walk around. That means politely asking family members to leave you alone till you're done. I've noticed that when I forget something its almost always because of an interruption of some kind. 

I do my round after readying departure, then she does hers. At first it was a "I won't see what you do" thing. Then I explained "That's exactly what I hope!". once she got that, that she looks at everything so different it's important it does, we haven't had a close call. She has caught a few items a few times (more than I wish to admit..). 

We don't move until each says "good to go".

Again, just us and how we do things...

Well, I did it. I forgot to raise my jack foot after hitching up the RPod. I heard some scraping when pulling out of my driveway, but had not thought to look at the jack as I was watching the wheels since I had pulled them off to clean the old grease out and add new grease. Somehow, it looked as if the one wheel had locked up, so I backed up and it seemed to be okay, so we took off on a trip. We got about half-way to our destination when we stopped and I looked and noticed the real problem.

I did a quick search, looking originally for a Camping World but there was not one on the route. However, there was a small RV place, Horizon RV Center in LaGrange. We stopped there so I could see about purchasing a replacement jack. They did me one better. They had some manual jacks in the shop area that had been removed from other trailers, presumably to install electric jacks. They let me take one for no charge. Even better, they loaned me the use of a reciprocating saw (aka sawzall) which made short work of cutting the leg so I could remove the jack from the tongue. The manual jack got installed, and I was able to transfer my Husky Brute flip foot over. It was a little worse for the wear, but was still in good enough shape and fully functional despite the dragging. I guess it cleared just enough so it was not dragging going down the road, just from the slope on my driveway.

We are now home. I measured, and I ended up cutting about 6" off the leg. I think I will square it up and see if I can drill new attachment holes for the foot, and then reinstall it. I will loose that 6" of lift capability, but I think it would be okay for almost all the situations in which we will be camping and it certainly would work at home where I have to level by lowering instead of raising the front end when the RPod is parked.

The moral of the story:  Check, double-check, and then check once more to make sure you raise the jack before taking off.