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I'm starting to get the urge make my pedalboard Midi'd so I can use more sounds with less stomps. I've got some very specific questions regarding using the pedals with Eventide units and was wondering if anyone had any first hand experience?

I have a 5, but I haven't messed around with the midi yet (I have a couple midi-compatible pedals and that was part of the calculus that went into the purchase) and I don't have any eventide. So I probably can't really help you. Hopefully someone else can.

That said, I would have no reservations recommending it as a switcher.

Not me, yet.
But I have a MIDI setup with 2 Eventide pedals and a DD-500 so I think I can help you
I'm guessing here that the ES-5/8 works like most of the MIDI controllers out there too:

1. Channel
2. Message
3. Value

Maybe my questions are more Eventide related than ES-8 related. If you've used a Factor pedal you know there are Bank and Play modes. I'm wondering it I can use MIDI to change presets but always revert me to Play Mode so I can use the flex and tap tempo in my PitchFactor.

If the mapping to that mode specific to the pedal is available via midi (or you can select a global "Play mode always on"), you're golden.

Not familiar with the Eventide specifics but know similar stuff for Alesis, Boss/Roland, etc.

With the Eventides you can map almost everything to MIDI. So the answer to your question is yes.
You don't need to change modes or even touch your Eventide pedals anymore.

What I do with my MIDI controller is something like this:

Page #1
switch 1: activate preset (PC command)
switch 2: activate preset (PC command)
switch 3: activate special function like hold/flex (CC command)
switch 4: activate another special function like tap tempo (CC command)
switch 5: change to page #2
switch 6: change to page #34

But things like tap tempo is something I want to have available on every page, I have an external footswitch that I can use like globally, no matter what page I'm in the controller.
You gotta check if you can do that with the Boss ES-5/8. Otherwise, you will need to map tap tempo and flex on every page where you want to use those functions.

The plan is to have the PF set up for master tap for my Space and TimeLine. I also just realized I can run Fuck/Rat parralel as my main dirt tone, the switch to series for those thick tones.

Well I'm sold on that feature alone. I need to get a bigger board and some money.

I'll report back.