Has anyone ever ran a vibrating jig with a weed guard? I am curious if they would run true in the water. Figure they would but wanted some input from someone with some experience 

I've never given it much thought. Most of my jigs are the Omega Rapture jigs and have never had an issue with weeds getting tangled in it.

Chatterbait project Z weedless. I personally do not own one, but they are out there and there must be a market for them.

If youre looking for alternative to the chatterbait freedom is the Pepper Custom Baits Rumbler. it uses a wide gap hook so you can hook the trailer weedless.

Yeah I saw the z-man one. I figured it’d be impossible to pull through grass but slow rolling around cover and not getting hung up would be dynamite! 

I've made them with weedguards and with screwlock swinging hooks to rig the trailer weedless but neither was as effective as a standard model. They function correctly, just not as effective for whatever reason.

Zman weedless.  Its not a weed guard...there are no such things.  It is a brush guard and it is vital if you want to skip into a laydown and come out the other side.  It takes serious concentration to not roll your chatterbait over when hitting branches and trunks.