Gosh Phreadd, that is a difficult choice.
On the one hand if you get a TW you will be quirky and unique, but will always have friends here on the Forum.
On the other hand getting the Super Sherpa addresses all the shortcomings of the TW you mentioned but now you would be riding near the bottom rung of a very tall ladder of conventional dual sport and trail bikes of ever increasing displacement, suspension and sticker prices with a seemingly endless array of aftermarket tires, parts, accessories not available to the TW.
In other words you have to ask yourself if you want the $10,000 KTM riders you encounter on the trail to think "What the heck was that?" or "Why doesn't he get a real bike?"
Seriously both are good choices depending on the intended use.