I think I have an answer to question 2. this is staight out of the ,akensis.htm file you should have:
This command will execute the specfied program and continue. Note that the file specified must exist on the target system, not the compiling system. It is recommended that you do something like this '"$INSTDIR\whatever.exe" /PARAMETER /2 ETC whatever.dat' (so that the double quotes ensure correct running, even if $INSTDIR has a space in it.
You have to put this (Exec as the command) and then the full_path_of_command_to_execute in " " in where ever you want it to run, but i don't know how to get two programs side by side hope it helps.