To stop having to log in each time with ssh there are some things you can do.
Vi/vim ~/.ssh/config and add:
Host * UseKeychain yes
Or you can be more specific:
host 20.30.40.* user myuser identityfile ~/.ssh/custom_id
To add to your keychain:
ssh-add -K ~/.ssh/custom_id
The -K means when adding identities, each passphrase will also be stored in the user's keychain.