Optocoupler and RF data

The signal you are passing through the opto is not RF the fact you have an RF transmitter on the output end has no baring on the situation. The MIDI speed of 31,000 (ish ) baud is a fast speed for an opto coupler and some types will not cope with it.

No the delays will not cancel each other out and you need carful design to a achieve what the data sheet says you can get.