I envision a small box with a couple of LEDs on the front for showing activity on the serial ports and then on the back a RS-232 connector, one connector for current loop from the host (which type for current loop? a DIN-6 jack?) and then a current loop jack for the ASR33.
It would then be possible to interface both a standard serial terminal without CL or computer and also an ASR33. The host is connected over current loop. The device does buffering of serial data so if the host is connected over 2400 bps there is some amount of buffering to allow for printing at 110 bps. It should be possible to have two terminals connected simultaneously. If I press BREAK on the ASR33 or the reader run gets activated the device type out a menu. This menu allows for selecting file to send, if the reader-run should activate the menu or not, perhaps setting baud-rates (auto-baud?) . Another feature would be to capture a file that is uploaded through the ASR33 interface.
To make it it easy I would design it as a small board that has a STM32 blue pill board. On the board there are level converters and current loop drivers. There would be a small transformer for a PSU that would give about +/- 12 V for driving the serial ports and current loop and then a 5V using a 7805. To connect to external jacks on the rear of the box there would be a number of headers on the board.
I prefer a crimped cable over a bulky flat-cable, but I can add a 40 pin connector on the board for connecting to the host. Then it can be a choice to populate this connector. Since the blue pill has USB built in it can be connected to USB if that is a wish, but it is not my main target.