TJ - win&win rests are fine. I've shot nothing else for years and don't have an issue with clearance - I suggest you look at a more fundamental level
Button being too soft is pointless - stiffen it up and move centershot in a bit if needs be. Make sure the shaft isn't also hitting the sight.
Clicker - you can buy purpose-made stick-on clickers, or any machine shop will tap a thread on the riser and recommend a suitable screw, alternative is the cavalier which mounts under the sight.
Archery World - tell his parents not to allow him to shop there unless he's with someone who knows what they're talking about (see other reviews of AW).
HTH