Hi - glad you are finding use in the program! As to your questions:

1. As long as the bot reconnects ok, it normally manages disconnects itself - which can happen. The bot needs to be set up. A good resource for that is here: https://discordpy.readthedocs.io/en/latest/discord.html

2. If you are not selecting an executable for your server (and instead a batch file), then you must tell GSM what the executable/process is that it needs to interact with via the "monitoring" tab - at the bottom. Click the "..." and select your "cmd.exe" - normally located in "C:\Windows\System32\cmd.exe". This is what batch files run. It's not the recommended way to do things, since the cmd.exe can be open by any number of other applications on a machine - and GSM cannot then distinguish between them - but it's totally do-able if you want to go down this route. Otherwise, it's normally better to select the server executable itself and add the commands in the relevant section there instead of using a batch file. Your choice, of course.

3. An interesting idea. I will add it to my list for potential improvements.