It's actually easier to create this problem than by bisecting a city, and the easier way is even more complex than bisecting a city.
You obviously can't put every hamlet, town and village into tzdb, for a lot of reasons. So, if you're trying to represent a time in a place that isn't in tzdb, you have to pick the nearest location that is in tzdb. And it's quite possible that between when you enter your time and when that time comes to pass, the location you were specifying for changes it's rules in a way that's different from the original place you chose.
If you bisect a city, you could create two new names, so that if you encountered the old name you'd know that something needed to be reconciled. But if you chose the nearest place and then your rules changed, you'd have no way to know automatically that it needed to be revisited.
For example, parts of Chile decided not to do DST any more. To support this, a new timezone, America/Punta_Arenas, was added to tzdb. Before this, if you were in Punta Arenas, you would just put all your times as America/Santiago. And now you have no way of knowing if those times are really supposed to be Santiago or if they were Punta Arenas and Santiago was just the best you could do at the time.
Location-based tz's are the best we can do right now but even still they have intractable problems when things change.