Well boys,
OP here. All of you that have done it and are willing to do it, on a T-dub or any motorcycle have bigger wavos than I.
As stated, we did the Easter Jeep Safari for 14 years in a row several years ago. We did Pritchet Canyon, Lower and upper Helldorado, Metal Masher and a whole host of pretty tough trails. There are some trails in Moab I would love to T-dub on. But that 5MOH AIN'T one of them. Based on what I see in that video, and the total strain it would be to ride ANY motorcycle on it, especially at 70 years old, nope, ain't happening.
In watching that video, even if I were to attempt it, the very first thing I'd do to the bike would be to seriously re-gear it. That is, especially on those monster adventure bikes, I'd have put a much larger sprocket on the rear and maybe a tooth or two smaller on the front. Waaaaaaaaaaay easier on clutch work while negotiating that or any trail with the same level of difficulty.
It would be interesting to watch a video of a T-dub on that trail. The Dub's normally got a whole lot less ground clearance than something like those adventure bikes so, I suspect the bash plate on a Tub would not be a pretty sight even 1/2 way through that trail.
Scott