i have many vintage midi devices linked to my interface via a midi router.
to prevent midi loops and extra midi info coming from drum machines and synths that i can't turn off, i usually disable track input when i want output and vice versa.
the problem i've had over multiple releases of ableton over quite a few years is that if i have an input device selected then want to go to select the output device, i go into setting, disable track input enable track output, go back to the midi channel in the project and output device is still greyed out, so i have to go back into settings again and double click the output setting (off/on), then i go back into the midi channel and then device is selectable.
midi input output device greyed out
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Re: midi input output device greyed out
I have had the same problem. As you say, the workaround is to do it twice, or close and re-open Live. I probably should have reported it but I rarely need to change my midi I/O it doesn't bother me enough to go through the rigmarole of reporting faults to support. Been there, done that, frustration ensues.