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Speculative Evolution of Diggers
There is a high chance that the diggers were the first mammals to ever enter the underland, due to the fact that they live underground in caves and first evolved in North America over 20 million years ago. The fact that diggers seem to be closely related to star nosed moles makes them the second species in the Genus Condylura. Moles eat insects, which appear to be everywhere in the underland and would have been a great food source for the diggers, leading to their giant growth and together with the high oxygen percentage in the air also to them becoming highly intelligent. 
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Origin of Fliers
The fact that the Appearance of Fliers seems to vary a lot makes it really hard to make out which Genus they belong to, but after looking through tons of pictures of Fliers and Overland bats, I was able to determine two different matches between Fliers and New World Leaf-nosed bats. The first identical trait is the fact that both tend to eat a large variety of food, covering fruits and insects, thus being omnivores. The other identical trait is their pointy noses. But due to the fact that leaf-nosed bats have been existing for 30 million years and that leaf-nosed bats have 55 genera and the Fliers do not really seem to perfectly fit a single one of those and tend to vary strongly in their appearance when it comes to color, exact nose shape and ear shape to a degree similar to humans, it is really hard to say to which genus they belong.
The fact that we know to which Family of bats they belong helps us a lot when it comes to tracking down their point of origin. We can say with almost 100 percent certainty that they entered the Underland somewhere in America, probably in the middle of the USA / near the border between Mexico and the USA. From there they started to evolve and later split into tribes. At this point in history some of them traveled to ancient Greece probably around 6000 years ago. When some of these Fliers later came into contact with the fliers in the Underland underneath the US these American Fliers adopted the naming conventions of the Greek fliers. This split into tribes is also the reason for the diverging appearances of the fliers. There also is a high chance that even today there are still fliers that do not live in the mapped underland underneath the US.
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Speculative Evolution of Fliers
Fliers entered the Underland far before the rats did, possibly even millions of years ago. Due to an absolute lack of predators or any danger for the Fliers they started to grow larger and larger, until they reached the size they have today. Their existence is also part of the reason why the underland has to have a higher density of oxygen then the overland, because otherwise the Fliers would not be able to breathe and fly properly. Like with the rats and most creatures in the Underland they evolved their intelligence from this higher density of oxygen as well. The ability to speak evolved due to the need to communicate and echolocate in larger areas and becoming larger as well, such evolving to make lower frequency sounds.
For their point of origin I will make a whole other post, since it will require a lot of research, because of their naming conventions.
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Speculative Evolution of the Gnawers
Due to a lack of predators the rats in the Underland evolved larger and larger, which was also caused by the lakes filled with food and the fact that for the most part the rats are the apex predators in the Underland. This growth and the higher density of oxygen in the Underland also caused the growth of the rats brain. Since the vocal cords of rats are normally able to act in frequencies humans can hear and also appear somewhat similar to our own, it is not too far fetched to say that the vocal cords evolved in a similar manner to our own. 
It is important to say that rats or atleast brown rats (which i will use as a base for the Gnawers, since they are the most common rat species in New York) were only introduced to America between 1500 and 1700 which would be far to late for the Gnawers to already exist in the modern time. But Rats existed in Asia for over 200,000 years, which could mean that the Underland or better said the Uncharted Lands stretch at least up to Asia and the rats entered the Underland somewhere in Asia. As time progressed some Rats wandered off to the Underland we know today, making their Evolution somewhat similar to humans with the difference that their point of origin is in Asia and ours is in Africa.
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