I think you cant move the config to context aware config rather you can use the context config in scheduler so that based on that config value your scheduler will get executed.
This is due to grid.less file not registered in your clientlib folder.Please add grid.less in ur css.txt of the base clientlib folder and check in your page view source if grid.less is getting injected or not.
Can you check the file through crxde whether its been replicated to publish from author or not. If it's present there then you should. be able to access the file directly from publish server.Are you seeing this issue with dispatcher?
@gspatil11 Few questions-1. Is it a fresh instance2. If not have you made any changes to trustore or keystore try to recreate the truststore and keystore.