@Ralf will have to confirm this, but I suspect the missing fills are just due to poor cleaning of the template. None of those missing fills appears in any of the drawing tools for the style. That list is full of things that don't belong there.

I think this is a limitation with using raster symbols as a symbol fill. You'll find the issue remins the same if you just draw a regular shape with the basic tools with that fill too, no need to involve a drawing tool. The issue here is that the symbol fill expects to be able to crop the part of the symbol that's outside the fill area, but that is impossible with images, because you cannot reduce them into lines and polys which you can chop into pieces like with vector symbols. The symbol fill fill style was defined well before raster symbols where a thing

Draw -> Symbols in Area is much more suited for this operation. It will even give you the option to randomly select from the grave group so they don't all look the same. You may need a couple of attempts to find the right values.

What Wyvern states is correct. That time is to allow it to become March 1st in every time zone.

Welcome choppinIt.

Which format are these maps in? If they are just flat images, such as scans of the original WWII-era maps, I don't think there will be any good options other than hand tracing then.

While Sue's method is a good general method for doing this, restoring the outline of entities drawn with a drawing tool is even easier. Just right click :CC2MCHANGE: and pick change like draw tool, Now, the command line prompts for a drawing tool. Right click inside the drawing window to bring up the list of tool, and pick the landmass tool. Then select the entity, and Do it. This restores the appearance to that of the tool.