You could do all that with powershell. A little sleep command, a text search through the running processes, loop until the first program launches, or you detect some sub process starting up, and then escape clause timeout before launching OBS, then even a further loop to see that OBS starts up and re-launch it if not.
And you could also use that opportunity to feed any command line launch options to those programs.
Powershell can more or less take any action a user might make by hand and then even more complex on top of it.
If you are interested in general IT or system admin type jobs related to Windows client or server, a great skill to pick up.