I had the Wadia 270/27ix combo. Sold it. To me, the 390S sounds better. Money doesn't always get you closer to the music.
The 31.5 transport will easily outperform the #37.
The 360s DAC and either the 31.5 or the 37 outperformed the #39. I've not listened to a 390s, but I've a friend in the business who does and has compared all combos and ranks them this way:
31.5 and 30.6 DAC
31.5 and 360s DAC
37 and 360s
Thought this might help!