Hi Scott,
I tested several solutions for CW keying and was not happy with the delay of the sidetone at SDR-Console (about 90ms delay).
Probably an issue of my Setup and Windows PC, but decided to go in another direction.
I am using piHPSDR as you and in two idifferent nstallations.
In both cases I use the buildin SW keyer in piHPSDR.
piHPSDR has to be compile/build piHPSDR with internal Keyer functionality,
My Installations....
1. simple RPi4b with GPIO- Connection is done via GPIO
- Config is possible (when SW was build with internal Keyer functionality) at the startup screen of piHPSDR
- 28ms delay from Key-Down to audible sidetone is very good. (see attached measurement)

2. Apache piHPSDR Console V2 with Midi_CW Interface
- it seem to be no available/free GPIO (not fully qualified)
- attached ext. Key via TeensyMidi Interface
You find more information about this at Christophs Website: http://dl1ycf.darc.de/midicw.htm - 30ms delay from Key-Down to audible sidetone is still very good.

FullBK keying seems to be not possible or very hard for the T/R Relais in Hermes lt2.
I would go with SemiBK and set a delay of 300ms.
vy 73 de
Alex, DK4FT