In '64, this might have been reproduced on a Xerographic photocopier, although it's also possible it was reproduced photographically (to produce offset plates) if they were making a large number. Either way I suspect it's most likely the "Star Trek" lettering was done by hand, but another possibility would be pressure transfer lettering.
I think you’re right about the pressure transfer lettering. Letraset was introduced in 1961, and it looks like their “Brush Script” font. This would have been cutting edge graphic design when Roddenberry wrote it!
Yeah, that makes a lot more sense. Thinking about it more it would be surprising to me if a commercial artist or draftsperson worked on this document and did nothing but the header lettering... there's a reason technical reports from this period with hand lettering or diagrams usually also have an illustrated cover. It's in for a penny, in for a pound on having a commercial artist involved.
