If you plan to play acoustically to any degree, go for a model with a floating pickup, since built-in pickups will deaden and alter the acoustic sound considerably. Can't beat Pete Biltoft or Kent Armstrong floating pickups for a good jazz sound - alternatively, consider a DeArmond Chieftain "monkey on a stick"
For a guitar, consider having a fully carved one built by Mr Wu in China. Over at the Jazz guitar forum (jazzguitar.be) you'll find some very happy jazz bunnies who have commissioned guitars from him - well within your price range.
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