Splunk is crazy, crazy powerful and fast. If you are lucky enough to work for a firm that can afford their licensing (so you can make some really advanced queries), it's an awesome tool to learn in depth.
Optionally he could mount the google drive directly with something like rclone
If you had old traceroutes, i would compare the path it is taking and see what is different about it.
I would also use traceroutes to see if maybe there is packet loss at one of the endpoints along the path. I'm not sure if there is something like pingplotter for unix, but a tool similar to that would potentially be helpful
In your frontend have something like
acl is_whitelisted src -f /etc/hapee-2.6/ipwhitelists/mywhitelist
mywhitelist would contain a cidr or list of cidrs
and then you'd have
use_backend rproxy_ssl if is_whitelisted