@UWPVIOLATOR If you can’t get the application to behave with respect to the restarts, you could always create a snapin pack bundling the executable with a script. In the script, you could check to see if the application was already installed and of the correct version, then if it wasn’t perform the install. if you wanted to kick off the application and then do something like loop while the executable was running, you might want to play with the start command, something like start "" installer.exe -args. https://ss64.com/nt/start.html
@george1421 the /k flag runs the specified command then leaves the command window open. https://ss64.com/nt/cmd.html