This second page explains what is happening to fictional Larry and the WASS employed ponies.
The central reason why fictional Larry is depressed is that he does not know how much time he will be spending as a pony or what problems he is going to deal with in pony society. The few times fictional Larry visited the magical land of Equestria, he was a diplomat and tourist.
Now, he will play the role of an immigrant and thus must deal with pony society. For example,
Pegasus ponies and Unicorns ponies consider Earth ponies to be country bumpkins and manual laborers.
Earth ponies and Unicorns ponies consider Pegasus ponies to be too flighty and intellectual lightweights for bona fide responsibility.
Earth ponies and Pegasus ponies consider Unicorns ponies to be wine and cheese aristocrats, incapable of doing the real work to maintain their unified society.