This system has 18 frequencies on site-1, has the ability to assign talk groups to operate in TDMA (Phase 2), which gives it 34 possible voice paths with 1 frequency assigned as the control channel. I was listening too, but didn't want to post much of what was said because sometimes things we hear are better off not posted since the ability for us to monitor isn't much more than a mouse click away.
I'll agree with some of your assessment however what is in dispute as you heard was that the CTA would join this system and the fear is it would overwhelm the capacity. I'm not sure how many frequencies can be added to a specific site, but the city of Chicago has licensed frequencies not even in use yet: WRAL 921. If I understand the process, since they're the licensee holders, could add frequencies from that license to site-1 much the way they did with unused O'Hare frequencies. The capacity issue shouldn't be much of an issue.
The "catastrophic failure, and everyone has an opinion now" comment probably was referring to something along the lines that they're operating on unlicensed frequencies that was overlooked and now belong to someone else so something has to be done sooner than later...or at least that's what I make of it. The "all we need is something on paper" could have been assigned talk groups by the OEMC and they could get the ball rolling possibly? I highly doubt they would lease a radio system from a private vendor when they have the 800 MHz available and is built out.
I looked up Kenwood portables, and didn't see any that operate in TDMA mode. This could be the other debate. Since the city is Motorola, this would require the CTA to purchase Motorola portables possibly? Writing up the RFP (Request For Purchase) was also mentioned, so it remains to be seen who responds. I'm suspecting CTA is required to put out any bids for new equipment like other city agencies and could take a little more time, or maybe not if it's the normal city vendor if approved.
They're going to finish their own testing on the 800 radio system, write it up that it works and after all the smoke clears, expect them to be using this system in the near future.