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I really have no clue what I'm doing wrong here! Help!

Thanks everyone! You definitely helped me fix the problem! I ended up ordering a separate power supply for my "Problem Child" :D

I'm away for one day and this thread blows up outta nowhere and I really appreciate that!
To answer some things brought up:

My board is definitely busy, but I like to mess around and since I'm away from home playing for multiple bands at my college (Contemporary Worship, Jazz, and my personal Rock band) I need some flexibility for covering different areas.

The WTDI isn't the perfect DI pedal for sure, and I agree that the design is pretty annoying with what it requires, but it still has improved my tone a LOT. That being said, I had to cut more bass than anything to get to a point where the notes I played were distinguishable rather than "thumpy" for the Contemporary stuff.

I really enjoy this online community, thanks again!
 
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I also use an adapter for the cable so it's center positive.
I'm sure this was the cause of your problem, using a "polarity adapter" on a common ground power supply. What can happen when you use one of these on a common ground power supply is that you end up creating a short circuit in the power supply chain.

The great majority of pedals are negative ground. When you use a polarity adapter to flip the positive and negative, and have a mix of negative and positive ground pedals, the + and - of the power supply end up shorting together through the shield of the patch cables. Don't use a polarity adapter on a common ground or daisy-chain power supply.

Using a separate power supply was the right solution.

There's a lot of marketing BS used to sell power supplies "isolated OUTPUTS" is not the same as isolated ground.
 
For starters your pedalboard has too much stuff.

Here's mine... Less is more

View attachment 3504595

Well, one could argue that your pedal board not only is too big, but also complete waste of space, the giant multi outlet power supply to that tiny pedal takes up about 1/4 of the entire board, not to speak of half the space on the board not being used for anything at all, in fact having a pedal board with just one pedal is totally pointless, why not keep the pedal plugged into a tiny 1 outlet power supply, take the pedal out of your bag as you would that board, put it on the bare floor and plug in the other end of the tiny power supply already connected to it.

It would be much simpler, much easier, and take up way less space, and it'll do exactly the same.
 
Well, one could argue that your pedal board not only is too big, but also complete waste of space, the giant multi outlet power supply to that tiny pedal takes up about 1/4 of the entire board, not to speak of half the space on the board not being used for anything at all, in fact having a pedal board with just one pedal is totally pointless, why not keep the pedal plugged into a tiny 1 outlet power supply, take the pedal out of your bag as you would that board, put it on the bare floor and plug in the other end of the tiny power supply already connected to it.

It would be much simpler, much easier, and take up way less space, and it'll do exactly the same.
The entire board is about a foot long. Hardly taking up any real estate. But you miss my point, I don't want to have to deal with any more outlets/ AC cables that I have to. Oh, and there are two pedals on the board, a compressor and a tuner, the latter also acts as a mute. (The tuner was added after the picture was taken.)