For lack of guidance I went ahead and changed all three occurances.
I still get a 404. But it seems to happen later on:
cf api api.10.60.18.186.xip.io --skip-ssl-validation
Setting api endpoint to api.10.60.18.186.xip.io...
OK


API endpoint: https://api.10.60.18.186.xip.io (API version: 2.56.0)
Not logged in. Use 'cf login' to log in.


cf login -v --skip-ssl-validation
API endpoint: https://api.10.60.18.186.xip.io

REQUEST: [2016-06-28T20:28:17Z]
GET /v2/info HTTP/1.1
Host: api.10.60.18.186.xip.io
Accept: application/json
Content-Type: application/json
User-Agent: go-cli 6.19.0+b29b4e0 / linux



RESPONSE: [2016-06-28T20:28:17Z]
HTTP/1.1 200 OK
Content-Length: 580
Content-Type: application/json;charset=utf-8
Date: Tue, 28 Jun 2016 20:28:23 GMT
Server: nginx
X-Content-Type-Options: nosniff
X-Vcap-Request-Id: 1444e97c-1562-46d4-6820-fe06d920e947
X-Vcap-Request-Id: 1444e97c-1562-46d4-6820-fe06d920e947::b7301932-6078-4334-82ff-46fa76d0032c

{"name":"","build":"","support":"http://support.cloudfoundry.com","version":0,"description":"","authorization_endpoint":"http://login.sysdomain.10.60.18.186.xip.io","token_endpoint":"https://uaa.10.60.18.186.xip.io","min_cli_version":null,"min_recommended_cli_version":null,"api_version":"2.56.0","app_ssh_endpoint":"ssh.sysdomain.10.60.18.186.xip.io:2222","app_ssh_host_key_fingerprint":null,"app_ssh_oauth_client":"ssh-proxy","logging_endpoint":"wss://loggregator.sysdomain.10.60.18.186.xip.io:4443","doppler_logging_endpoint":"wss://doppler.sysdomain.10.60.18.186.xip.io:4443"}

REQUEST: [2016-06-28T20:28:17Z]
GET /login HTTP/1.1
Host: login.sysdomain.10.60.18.186.xip.io
Accept: application/json
Content-Type: application/json
User-Agent: go-cli 6.19.0+b29b4e0 / linux



RESPONSE: [2016-06-28T20:28:17Z]
HTTP/1.1 404 Not Found
Content-Length: 124
Cache-Control: no-store
Content-Language: en-US
Content-Type: application/json;charset=UTF-8
Date: Tue, 28 Jun 2016 20:28:24 GMT
Server: Apache-Coyote/1.1
X-Vcap-Request-Id: a43cdd2a-1c0f-4f8d-7439-8174c88c7fde

{"passwd":"https://console.10.60.18.186.xip.io/password_resets/new","signup":"https://console.10.60.18.186.xip.io/register"}


API endpoint: https://api.10.60.18.186.xip.io (API version: 2.56.0)
Not logged in. Use 'cf login' to log in.
FAILED
Server error, status code: 404, error code: , message: