Oh, I guess I can see how it would be if you had a tone sucker like an original crybaby...I have always preferred the Vox type wah myself as they always seemed to hold up better than a crybaby...But in the end just for me, the end result isn't worth the hassle...But that is just me...I can totally understand a player wanting a particular pedal of any kind...It might be the tone, the feel of the pedal, the button or maybe the reality is that it's just an audio placebo that doesn't make any real difference other than it makes the player feel better...That's important...

In terms of gain matching...try to get the level with the loop engaged in the spot you want in the chain to exactly match with loop disengaged...that's about all I can think you can really do to...You could put it out front which is a typical approach...I wonder if this one is sucking tone out like a stock crybaby does...From what you describe, I am getting that impression...not sure...thinking out loud is all...

I am just taking a guess, but I wonder if you like the feel of the pedal under your foot? if so, something you could think about would be modifying your wah pedal to work as an expression pedal...just a thought...You can use the digital wah models in the HD and have the feel of the real pedal...just thinking out loud...