On the flip side, it's pretty cool what Emacs can still do on a text terminal. Multiple windows, mouse, auto completion pop-ups--all work comfortably over an SSH session.
There are quirks, I'm sure. But that is one that actually makes sense. I do sometimes wish it were easier to cd to the root of the remote, but not often.
I usually prefer having the main remote directory open in dired and a shell session in another buffer. I prefer to work in a Posix shell as AFAIK eshell does not do at least one of: IO redirection, piping.