Mostly, you want to keep the tone as clean as possible for a traditional jazz player. Most jazz players play at a more reasonable volume level as well. Do you have a mic he can use? He probably has a fairly small and portable amp that he's used to using.
Another alternative is a simple direct box that includes speaker simulation like those made by Behringer.
Or, run the guitar direct to your mixer or interface and add speaker simulation using a convolution type reverb plug-in, like Perfectspace, Acoustic Mirror in Sound Forge, etc. There are lots of impulse responses either shipped with plug-ins or available online that are impulses of actual speaker cabinets, 1x12", 4x12" etc. Load one of those in and it will shape the raw guitar signal quite a bit.
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