Occasionally (every 4-8 attempts), the server will crash when a user attempts to connect. The server hangs after the initial Authenticator check and user joining the game message, at which point a minute later it is killed by the watchdog for no ticks in 60 seconds.
This began occurring on September 13 (well after the update to 1.8 full release after running snapshots since the server's creation). I have 20 crash logs related to this issue.
I have attempted moving the playerdata files so that new ones are forced to be created as a way to resolve the issue, but it continued to occur.
Attached is the most recent crash log as well as a screenshot of the server console at the relevant time.
Related issues
duplicates
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Dupe of MC-63590

I can't really agree that this is a dupe of MC-63590 as this occurs when a user logs in and is just being masked by the watchdog; the watchdog isn't the cause of the issue.

Watchdog is watchdog.
Your crash report:
Description: Watching Server
java.lang.Error
at java.util.ArrayList.indexOf(ArrayList.java:298)
at java.util.ArrayList.contains(ArrayList.java:281)
at java.util.ArrayList.batchRemove(ArrayList.java:700)
at java.util.ArrayList.removeAll(ArrayList.java:671)
Crash report from MC-63590:
Description: Watching Server
java.lang.Error
at java.util.ArrayList.indexOf(ArrayList.java:298)
at java.util.ArrayList.contains(ArrayList.java:281)
at java.util.ArrayList.batchRemove(ArrayList.java:700)
at java.util.ArrayList.removeAll(ArrayList.java:671)
Also, MC-68366 and MC-68948 reported having this very same issue occur. Sadly, the only way to fix it is by turning off the watchdog via max-tick-time in the server.properties.

So having the server hang (potentially indefinitely if I turn watchdog off) when someone logs in isn't a bug?

Not sure. Please attach a server log showing this with the watchdog off.

I will as soon as it occurs again - it's not consistent in when it happens.

The server watchdog shuts down the server if it hangs for some time, see MC-63590 to enlarge / switch off the timeout value.