PROBLEM SOLVED.
I decided to take another look at the compressor assembly while going through the diagnostic testing. As mentioned before, the system seemed to be fully functioning up until the air pressure sensor called for the compressor to engage. Unbolted the assembly once again, supported it, and double checked all the electrical connections within the assembly. The good ol' "grab each wire to make sure nothing is loose" trick actually worked. While tracing back the two power wires (Connector C2 - Assembly Air Suspension Compressor Feed; Orange/Brown wire (Y40)) I found that the brown wire was physically disconnected from the air compressor body. (photo attached) The positive wire was not long for the world, ready to break off.
View attachment 126172
The connection to the air compressor itself is pretty bad... this truck is a 2014, meticulously washed but get this connection corroded itself off the body. Note that there is NO post style connection, it appears that the connections are potted at the factory, which is a process of embedding the connection into the black resin seen in the photo. As a test, I started the truck and held the wire to the connection which immediately started the compressor once the sensor deemed necessarily. Truck lifted off from the bump stops as the bags filled. Rechecked the system with the scan-tool, and retrieved data from the ASCM, with a reservoir pressure now at 125psi (up from 38 psi prior.)
Now the fix. As I do not want to "bench repair" the connection, requiring the system to be disconnected and bleed all air from the tanks and bags (which according to ALLDATA, required recharging with Nitrogen by the dealer.) I am planning on re-soldering new wire pigtails back onto the compressor body to sit within the existing potted cups shown in the attached photo.
View attachment 126173
I am hoping that this entire process can help others in a similar situation. We know that a valiant attempt at fixing issues with these trucks (or any vehicle for that matter) without heading to the dealer is the best move if mechanically inclined. I offer anyone to PM me with any similar situations and I can help as much as I can - sure learned a ton about these systems from this.
P.S. - The air system on the 2500's are certainly an open system to the atmosphere - proven by the ability for my previously depleted system to regain pressure through the on board air compressor without recharging through the reservoir. Cool system, but honestly a PITA when there are issues.
Cheers all.