For what its worth, I was just going through this with GINA on Mac using some newer crossover builds. I had to use SAPI winetricks, used dotnet 4.8, and installed the voices from
http://espeak.sourceforge.net/ and they were working. The issue I have however is that it doesn't look like my log file is actively parsed, so no triggers ever fire, although I can search the logs fine and it shows it should trigger.