That was made for the book Star Trek Chronology: The History of the Future, I'm not sure but I think Greg Jein built it. The first pic you posted was used to illustrate the Federation/Romulan war.
A few. That's where the Daedalus model first appeared, and the Columbia mentioned in Where No Man Has Gone Before. They did a lot of conjectural stuff, like a pic of Robert April which was Gene Roddenberry in a Pike type uniform.