The Peachtree Deepblue2. Amazingly good portable with wifi/Bluetooth and an aux jack.
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The Audio Engine HD3 would be worth a look. They're wireless, easy Bluetooth hookup for internet radio, and he can just plug his CD player right onto the speakers since they're self powered and he'd be all set. I'd think this would sound much better than Bose and at $399 they're well within budget. Best of luck.
I recently bought my 3rd Deepblue (1 version 1 and two 2's) as a gift for a friend. After about a month it just crapped out. Since it was still under warranty I contacted Peachtree, described the situation, and was immediately sent a work order.
Just for kicks i asked them if they had any plans to sync with the now all-over-the place Amazon Echo - since the DB2 is Bluetooth and the Echo is wifi they ain't presently sympatico. I use the aux jack since I found the Bluetooth connection experiences annoying dropouts, etc.
I listened to the Sonos Play5 speaker and, while a very okay speaker, the DB2 is a far better and cheaper speaker. Way better.
Peachtree said they will be releasing a DB2 "SKY" in early 2018 which will offer a wifi connection. Woohoo!