I started by opening up the vectorized file I chose (NASA.eps). It consisted of one visible layer.

Click the v symbol in the layer and you'll see dozens of design elements that make up the logo. 

Decide on the Layers

Given the elements, it made the most sense to use the following layers:

Silkscreen: White

Soldermask: Blue

There was not a red available. So I made the design decision the "swoosh" would be bare copper (actually ENIG, discussed later). It'll look more gold than red but it adds to the PCB nature of the project.

I set up the layers per the Gingerbread convention:

Front SIlkscreen: F.SilkS - for the white elements

Front Copper: F.Cu - for the swoosh and under the silkscreen and soldermask parts (essentially the whole board)

Front Soldermask: F.Mask - Due to Gingerbread and KiCad conventions, the soldermask is specified where you DO NOT want soldermask. This would be any visible parts of the copper "swoosh" but noting the white lettering (and hence some soldermask beneath the silkscreen) covers the copper.

Arranging Elements

Make new layers in the drawing named F.SilkS, F.Cu, and F.Mask.

Start by moving all the star elements, which include the triangles ("star rays") into the F.SilkS layer. You can move the N and first A in that layer also.

The S and the last A are broken by the bottom part of the "swoosh". If they are not already in parts, trace the individual parts so you can put them in the F.SilkS layer.

The Swoosh copper should not have blue soldermask. Trace the parts that include the parts of the swoosh that correspond to areas that cover. You can add the entire swoosh then use the Subtract tool to get these traced items to not have soldermask removed. Yes, it seems backwards but you can import your intermediate file saves into Gingerbread to see how it's going. Most designs are not this complicated.

The last silkscreen item should be the ellipse. It is broken by the Swoosh too. So make it with the main ellipse and the part below the bottom part of the swoosh.

Making Light Holes for LEDs

The two large stars in the top portion of the logo is where I wanted LEDs to shine through. I took perfect circles centered on the rays and put them into a layer named Drills. The rest of the LEDs are handled on the back side.

Next: to make the footprint in Gingerbread.