Having owned both, I can honestly say that the Timeline beats out the VMSD in more ways than one. Just a better overall sound, much more control over the parameters, digital BPM/MS readout, full midi implementation, more in depth looper, several more delay engines/modes, 200 presets compared to the VMSD's 8 presets... Just beats it out in every way but one - simplicity. If you want to keep things simple, yet have superior delay tones, the VMSD can't be beat. Other than that, the TL blows it away IMO.
+1. I've had both as well.
Oh, and in terms of resale, you'll lose a lot with the Empress. You won't with the TL.
Both given 6 months will drop in resale value once supply catches up.
I think they are both great pedals, the real question is how complex of a delay you want operationally. Menus? Go Timeline. Grab and go? VMSD.
Had both also. Love the VMSD, but the TimeLine is tops in terms of features and the feel of what many people do not appreciate, the analog dry path. I saw it visually on wav files when I compared the VMSD to the El Cap.