Hi,
Could you add a check button in the toolbar, labelled "Open COM Monitoring after upload",
that will start automatically the COM Monitoring window when transfer to Arduino is completed ?
In the same way, why IDE systematically recompile the project when we click "upload 2 arduino" ?
If nothing has changed in the source files, we don't need to recompile the project, just upload it...
As there are 2 buttons, (one to compile, one to upload), we just need that "Upload" just "Upload" 
Regards.
Chris