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This is a 6.0L diesel I assume? Won't start or won't crank at all? And I'm assuming it's an automatic transmission.
What it sounds like is that you have either a loose connector or a broken wire in the bundle that you are fooling with. The only thing you're probably going to be able to do is to carefully move one wire at a time without moving others until you find the one that will let it start. You're probably going to need a helper.
Before that, though, I'd push all the connectors in the area together to make sure they're fully seated. And I'd give a little tug on the each wire at the back of each connector to make sure none of them are loose.
My '04 had the overdrive button wiring harness replaced in '06 due to wire chaffing. This is located in the column near the gear shift. This might also be causing your issue.
It is possible to tighten them but difficult to describe. Determining wether the pins in the connector are loose in the receptical or the wires are loose where they connect to the pins is the first step. If the wires are loose the metal pin can usually be removed from the connector by sliding a jewelers screwdriver in the back of the connector, unlocking the pin and pulling it out of the back of the connector shell. You can re-crimp it or use a touch of solder to repair.
If the pins are not making contact where the go in the receptical, unlock the the wires as previously described from the receptical half of the connector and slightly bend the now exposed tab to create more friction when the two halves are put back together. This is all kind of delicate stuff. another fix would be to cut the wires just behind each side of the connector two at a time so as not to mix up which ones to connect together, and replace the whole thing with a couple of generic crimp-on single wire connectors from the auto parts store, or even use butt splices.