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I've had Delaylab and Headrush. I still have Headrush.
If you've got another top-notch do-everything delay, I can't think of a reason to keep the Delaylab. My favorite thing about it was that it got weird with expression pedals. In digital modes, it made the computer lose its mind. But I think most multi-function delays can do something similar. I got $130 for it on Reverb.
The multi-head mode on the Headrush can be set to make nearly random repeats in a way I haven't heard from anything else. The way that you can adjust the time between heads doesn't seem to be replicated on other pedals. In most other regards, it's a very frustrating pedal and I wouldn't keep it if not for the multi-head thing.

I do like the multihead mode on the Headrush. I should probably see if I can duplicate it in my rack stuff before offing it.

I love the Headrush as a looper, it just has the perfect looping interface in my opinion. The multi-head stuff is fun too, but I do wish you could add some grit to the delay sound. I really only keep it around for looping. I also have a DL4, DD5, Timeline (also RE20 and RV3)...

Since you're planning to keep the iStomp, maybe sell both the Digitech Delays and keep the Vox? Gives you the most tweak-able delay options from one pedal, and while the looper may not be amazing, but it certainly beats out the others. I just don't know how much of the DigiDelay's weirdness the iStomp captures.

Am I the only one that thinks it's funny that Digitech, a Samsung company, makes a guitar pedal designed to interface with apple products?

Just felt like putting that out there.