So yesterday about ready to toss both the MacBook air and the thunderbolt dock in the trash I returned to the process I used at Apple in the 90's as an internal help desk tech.
I disconnected all of the peripherals attached to the dock. The dock then connected and disconnected just fine without the ejector app.
One by one I started adding the devices back starting of course with the 4K TV I use for a display ( I know bad Idea but I committed)
After adding each device while connected, I would simply unplug the dock and plug it back in.
External G Drive 8TB External Power Supply
The offending device is a thunderbolt ready hard drive by G Drive. It is the 8TB work drive I store video being edited for the next episode of CoolToys TV. There isn't anything else on the drive but it regularly hits 7tb of data with 4K video. So I moved everything to the main server, and tested again. Same problem, not storage volume related.
If I power the 8TB G Drive off, connect to the dock and then power on the external drive, all is well. This is regardless of use of the OWC ejector app.
4TB Portable G Drive
My first guess was the larger G-Drive went into power save mode and spun down, causing some sort of error on reconnect. I have a self powered 4 TB drive that did the same thing, however it did act differently if I used the OWC ejector app. If I use ejector on the 4TB USB powered drive, about 50% of the time it would reconnect the dock just fine. If I eject the portable drive, physically disconnect and reconnect, the dock is working normally.
This is new since Ventura, so I can't tell if it is the new Ventura USB drivers or the OWC cache does something funny when the dock is disconnected and a drive goes to standby. Not sure why the 50/50 with the portable drive.