Here's the basic layout of the shop. The circle with an "x" in it represents a ball valve.
Below is a pic of the chart in ThingSpeak. The slopes of the different curve segments are calculated below:
So it appears the best the system can do is around 2 psi/hr. That's with as little of the system as possible in the mix, i.e. best case. That said ,there's still the compressor check valve, a water separator/filter, air line quick disconnect fitting, and 3 ball valves in the mix. It's possible the air line quick disconnect fitting could be the bulk of it, however the filter also has an auto drain feature which could be leaking too.
UPDATE: I've been opening up each end point separately and it looks like the Bridgeport is kinda a problem. I'm pretty sure it's the Kurt Power Drawbar IN/OUT switch - I knew it was leaking, but it's leaking more than I wanted. I think the rest of leaks are probably a collection of minor things I'll have to find by soapy water, etc.