Well, about singing (or non-singing) angels...
This is a topic which I’ve found polarized beliefs about on various apparently reputable Christian websites.
It seems to me there are two broad schools of bible interpretation — the airtight-proposition school and the modus-operandi school. The former is driven by fear that one might do something wrong, the latter by hope and love and joy. The former says that angels probably don’t sing, the latter says that angels almost certainly do.
“Would Jesus wear a Rolex” is a modus-operandi question. Whatever use Jesus would make of a Rolex, it would be to the glory of God the Father. WWJD is very context sensitive. There are some contexts where a thing would be hideously wrong, and other contexts where a thing would be just fine. Ostentation is not Jesus’ style even though He could muster all the heavenly bling He wanted to. He just doesn’t want to.