However, upon listening to ED-E's recordings, carefully, I came across him (it?) saying this:
"If you are listening to this from one of our Chicago outposts,..."
For as long as I had been playing FO:NV, I had been expecting the Enclave to be the size of the the Mojave BoS Chapter outpost. However, after listening to the recording, I now believe that there seems to be a string of outposts that the Enclave posses, maybe not too many, but a few. That would seem to point to the Enclave in Chicago to be somewhat stronger, in comparison, to the Mojave BoS, even if just slightly. And Navarro is described as just a outpost in the same recording, so Outpost does not mean small from my understanding...
Perhaps the Developers putting in this line was intentional to set up the scene for the next game? I have also heard that Caesar mentions BoS Scribes being caught to the East of Legion Territory, and Bethesda defending FO Tactics as Cannon.
Maybe the Compass is pointing to Chicago for the MW BoS and the Enclave to meet...