If this is not long enough, it makes sense to get use of the RS422 approach (bipolar Rx/Tx line). There are converter chips available, e.g. from Maxim: MAX489E, which should work, but I never tried this chip by myself…
Yes, you have to assign different MIDI channels to the MIDI outputs. This can be done with the mk_midio128_syx script
Monitoring would only be possible if you would use DINs which are directly connected to the DOUTs. In addition, a special software would be required which is able to request the DIN values, and to compare them with the DOUT values.
I don’t know which software is ideal for your plans, but I guess that any MIDI sequencer could be used.