I have a PR out for TS-3072 "Debug logging for a single connection". https://github.com/apache/trafficserver/pull/350
So far there is general agreement that this is a useful feature. However, there is contention on how this feature is activated. The current proposed implementation uses the existing debug.enable config in records.config and adds a debug.client_ip option. Some people feel that we should not be cluttering records.config with another entry. And it should only have a plugin interferface. However, to get the debug logic to trigger early enough to capture debug messages for the start of the connection, we would need to extend the pre-accept plugin hook to include TCP accept as well. This would probably push the fix into next year (unless someone else takes it on).
Then to get the behavior of enabling the IP address on the fly, someone would need to write a plugin that watches it's config files for changes (or some other dynamic communication mechanism).
If you have an opinion one way or the other, add a comment to the PR (since there are already quite a few comments there), or reply to this thread.