A sailor's museum has many of Scovill's old button dies. https://www.marinersmuseum.org/2016/12/button-button-whos-got-button-die/

Kinda looks like that German aviators group that was used as a front to train pilots in Germany before WW2. 

Ha! Does Matt know his background?!  Matt is the Wizard of Research with that stuff 😁.  mikie

I just received this one, legitimate as far as comparisons go. It is the first one I had seen for sale or auction.

WW2 army em buttons had a certain finish and a low relief, but these Waterbury buttons have a shiny edge and the backsides are indented a bit, something usually on post-WW2 buttons.   These appear to be on their issue card.        

Nice cap! It’s in much better shape than the wreck of a one I bought this weekend. It was so sad looking I just had to bring it home. I did a little research on it the past couple of days. I was told the change in the badge mounting happened around 1947 ( or also 1949) with a regulation change. The back of the paper name tag is dated 1944. Unfortunately the name is illegible.  mikie

You might try using a UV flashlight in a darkened room on the writing.  I have found that some inks will glow under UV light.  You can get a small UV flashlight at Home Depot or Lowes.  I originally got mine to look for Tomato Horn Worms on my tomatoes at night.  The worms glow under UV light and are a lot easier to remove that way than trying to find a green worm under green leaves in daylight.

I would agree Colt's definitely sell at a non-insignificant premium. I regularly find RR 1911s much cheaper. Also I have found that Colts that have serialized slide sell for even more. I would guess because you can verify the slide and frame are known to be "correct"

I collect the Naval ensign flags (among far too many other things) I will say the most common one I have encountered is the #7, which is just a tad smaller than yours. the #12's are the smallest and fairly sought after. The bigger ones are harder to display (bit more fun at parties). Interesting yours has rope instead of grommets.

The barrel is good. Clearly used but not abused