Scott, I think that, unless you are capable of performing the sound at least as well as this player, worrying about the quality of jazz guitar sound is moot. And if you CAN perform as well as this, well, firstly, I would LOVE to hear some of your work, and secondly, you probably aren't worried about your current jazz guitar sound in the least!

As with most imitative synthesis, a better sound can only be a help to the better player. If you are not phrasing and playing idiomatically as well as this performance, all a better sound does is accentuate the shortcomings. You play a T2 still, right? Some of the SA tricks can help you sound MUCH more idiomatic (by switching the legato/staccato and fret-slides in and out based on your phrasing). The Sound-font format does not have this ability, and correct me if I am wrong, but you can't make your own sample-based SA User Tone, can you?

Basically, though, yes, it's a great sound, but unless you can perform it as well as this guy, you are going to be as unimpressed with it in your own hands as much as any other guitar sound you have.