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So here we go with heavier gauge wire... I have no idea how that's going to help, but I'm out of options until I get my hands on an oscilloscope.
Lets try this thing! I've got some more four strand... if nothing else, at least it'll be colorful.

'Time Consuming' is not nearly descriptive enough. I'm using the motherboard and cartridge port I originally started this project with.

Drum roll please!

Beep Boo Boop, we're fucked. So that doesn't work. Let's try wiring up the new cartridge port.

Welcome to my nightmare.

Now I have everything hooked up and ready to rock. I honestly don't think anything's going to happen, but let's plug in Zelda and giv... Dafuq!? IT WORKS!!! Holy Shit!

ZOMG! Let's try LSDj...

Shit...
Well, I guess it's better than nothing. The mighty oscilloscope will offer me more answers this evening.

After carefully reviewing pretty much every DMG schematic on the internet, I think I can safely say that the length of the ribbon cable has nothing to do with my problem. After consulting my old man, I have come to the conclusion that what's happening is there's some contact problem along the system, and the higher addresses aren't being accessed.
For example; here are some of the games that don't work at all (save for Zelda, but that can't be played, so we'll call it "not working")

Here's an example of address lines not being accessed. Gex plays just fine on my gaming DMG.

But when it's plugged into the keyboard, it glitches heavily, and doesn't boot.

Now here's some games that play, but are heavily glitched (graphically). Again, they play perfectly fine on my gaming DMG, but look hella messy on the keyboard. Ninja turtles is interesting, as it plays just fine until a bad guy is on screen, then it freezes and dies.

You little bastard. What are you hiding in there?

I suspect that I may have warped the old cartridge port or the pins while working on this thing (I've been bending pins and soldering on it A LOT).

So, I'm just going to replace it. We'll go ahead and use this Prosound DMG. Don't worry, it's the first one I built, so the mod isn't that great, and it's parts are going to the greater good.

I have this weird feeling... like I've done this before...

Okay. Let's test it...

Hmmmm... so, now it won't make it past the BLING! This is kinda interesting. Well, I'm already through the rabbit hole on this one. Let's swap motherboards!

This morning feels like constant Déjà vu.
Let's try it out.

Damn... more of this bullshit.
Time for lunch and then I'll check my wiring. I suspect this hangup is actually my fault.

*sigh* I rewired the whole thing. Still doesn't work, but there is progress: Both Pokemon and Link's Awakening bleep and bloop before not booting.
Again, the only games that don't work are the ones that have a memory bank. I guess the wires are too long.
Well, this complicates things a little bit. Not sure how I'm going to solve this one... guess I'll go study some DMG schematics (it's probably something stupid/simple that I overlooked).

Thanks man. I figured my ribbon cable thing went WAY too smoothly.
I'll let you know what I find out.

Apparently, coffee and a burrito turns me into a dog.
Here I am, hard at work.

Here's a little more wiring action!
Remember: Shrink tube IS your friend. Electrical tape will stab you in the back.

Yay! The sound works (not that I had a doubt)

Awesome, now lets plug in LSDj and... wait, what? WTF is this?
You were just playing Tetris...

Lets see if you play on the other DMG...

Well, I'm stumped. Alright people, any thoughts?
It plays every other game I have (I checked all 127 carts) but LSDj wont boot. WTF?

SNAP! You're right!
I know where I'm buying those from now on.

Shall we get back to the build?
So, after two days of WAITING FOR GLUE TO DRY, I get to wake up to this:

The glorious thing about electrical tape is that you stretch it tight to hold something down, and it will never relax. I gives constant tension.

Let's peel that off and have a look.

I gave this thing a good hard twist, and nothing shifted. Looks like we're in business.

"Amazing" you think "Now we'll finally get to see some real magic happen."
Well, you'd be wrong... because there's STILL MORE TO GLUE! Nothing major.
Witness exhibit A.

Those need to be bonded together so we don't suffer any further structural failures.

This is my favorite PVC cement.

Give him the Clamps!

"Oh no!" you think "We have to waste another day WAITING FOR GLUE TO DRY?"
HOGWASH!
I have the base back, so I can work on some wiring... and wire is one of those things I definitely have at my disposal.
See; when your dad's been an electrical engineer for the last forty years, and has worked in places from Atari to Creative Labs, there tends to be a TON of spare parts laying around. Especially wire.

I think I'll start with my 1/4" stereo jack and a length of 4 strand.

I yanked out the green wire (because I don't need it)

No real place to put shrink tube, so I'm just gonna leave it naked.

Then I did the RCA jacks. It was essentially the same as doin... WTF? Shit, you're not going to believe this.
(I wish I could blame this on weed)

Anyway, after some swearing and calling myself a dumbass, I fixed that problem (it's always important to pay attention to what you're doing) and installed the jacks back into my "Window of Truth".

I think it looks cool from the outside.
(picture doesn't depict levels of radness)

Now my desk is a mess, I'm out of coffee, and it's time for lunch.

Then it's time to learn some more LSDj before getting back to work. Oh, and this is my little retro corner for games that have to be played on a CRT television set.
(Note: I haven't taken a picture of a TV since the early 90's when I was sending in high scores to Nintendo Power)