For a reasonably loud easy to carry general purpose amp I'd recommend you try a Cube EX.
Fifty watts, double 8" drivers, dual tweeters, true stereo effects, pole-mountable, two independent channels, auxiliary inputs, and can run on batteries if needed. There are amp simulations built in, but they aren't considered very usable by most guitar players. Since your son plays jazz, the true stereo chorus is the same that propelled the Roland Jazz Chorus amp to fame, so "jazz" is built into its DNA.
A lot of people busk with these and love them.
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