Dear Silens,
First of all, thank you for interesting my CSV Advanced extension. Regarding your questions:
1. No, CSV Advanced does not support cron-job. It requires admin to log into back-end side and manually upload CSV file for importing.
2. Yes, if you give url of image from another server, then CSV Advanced will download the images and put to your server and assign for corresponding products.
If you have any more questions, please don't hesitate to let me know.
Sincerely, Giang