Sweet, we're talking guitars now I'll give my humble opinions....
I wouldn't go with a T5 for blues...the T5 is basically a competitor of guitars like the Anderston "Crowdster" and the Gibson SST chet atkins (maybe not so much the SST), basically it's good for people who want to be able to switch between acoustic and electric sounds on stage without having to switch guitars....or its good for acoustic players who want to dabble in electric...cool guitar but with a T in the stable you don't need it.
I'm with others on Gibsons...I wouldn't buy anything newer and the custom shop stuff is way to high. Perhaps you could find something older and play with the setup....
Another thing that you might consider (though pricey) is that custom jazz guitars have become a pretty hot botique market as of late...that means that there are lots of copy cat guys looking to get in...you might want to check that out.
As for what's left, I say do the same thing you would for any other guitar...look for what "speaks" to you. Only you know what "sound" you are looking for. if you want to completely match a musicians sound, then just google thier setup and you should be good to go. One other thing...for jazz the amp seems to be as important as the guitar...you might think about what your going to do in that area as well.
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