Will this work

I am planning a board that has RS232 half duplex communication. I will use pins 2,3 of a pro mini for this. I want to be able to debug the comms through 2 and 3 so I came up with this plan. These are very close to the components I will use but this is not the exact design:

Will this work ok when the IDE has to reprogram the Arduino? I know there will be many rules. I will need to use half duplex in and out of 2 and 3 plus not do any hardware serial writes if 2 or 3 has any traffic.