I’d recommend something with "shortcut" buttons - so you can set up some favorite playlists or internet radio stations that he can easily turn on with the push of a button.
My 5-year-old son really likes our AudioPro C3 speaker - very easy to use with 4 shortcut buttons. Also rechargeable battery allows it to go outside. It also has "two speakers" ;)
When i was that age i was jamming to my favorite James Taylor tape (JT) in my fisher-price tape player all day and night.
And to answer your real question - yes you're crazy. Love for children makes people do crazy things.