The orange wire that connects to the rear stud of the lighter receptacle is so loose, I can disconnect it by blowing on it. any tips on how to make that a tighter connection? I'm afriad to crimp the plastic connector... doesn't look like it has a lot of elasticity.

you gotta squeeze down on the connector a bit to tighten it with needle nose pliers.

Drop of solder.
If u want your radio to go while ignition is off, this is a good place to connect it