I would install it with docker (moreover docker compose) preferably. Easier to maintain and troubleshot. Anyway, for 1, make sure jellyfin has the rights to see your video and music folders. For 2, are you trying to do it from the same network or from outside?

Maybe take a look at paperless-ngx, it will take care of the OCR for you and make it searchable. Just not sure if it will show the path correctly.