The only way that can happen is if the operator at the Dane County comm center has the MONITOR SWITCH activated for that repeater. This is easy to do accidently on some consoles and may go un-noticed. Having the MONITOR function activated opens the input frequecy up to any carrier on that frequency irregardless of PL tone, especially if it is an older system and safeguards are not built in to the system to keep the operator from bumping that switch inadvertently. Most consoles that I have installed and maintained in the past do not even have the MONITOR function availabe at the console - only at the site of the repeater in the equipment room for TEST purposes. Some Ham repeaters have this feature built in as well for carrier activation OR PL activation as a selectable option.
In this case, based upon the FIRST posting in this thread, I believe the person receiving the paging on 154.400 with a portable in the vehicle is actually hearing a direct transmission; not from a repeater locally. The SIGNAL STRENGTH of that transmission can be determined in a couple ways as well as to LISTEN for a squelch tail of a repeater timing out after that weaker signal stops. If there is No squelch tail from a repeater being triggered from a distant station, then it would usually be a direct reception. And if that is the case, we are back to square ONE in trying to determine the origin.
Question for BigLaz - do you hear a strong repeater timing out during these pages or is it a primary weak signal that you are receiving? If it is a primary weak signal, do you receive it better during hours of darkness than at mid day? This is also an indication that it is a distant direct primary transmission because due to ambient background noise being higher during the daylight hours, this will affect the signal to noise ratio. As an example - I can receive Thunder Bay Ontario on 142.770 from Green Bay at night with the 14DB beam pointed in their direction... that's just under 300 miles away. As soon as the sun rises, that VHF signal is long gone until after sunset again.