And here is how the award sequence would look like:
IC 2nd class:

IC 1st class:

U-boot war badge
Couldn't find an image. Probably a revised version of the WWII award would do the trick, though
Hanseatic cross:


I used the one from Bremen, since IMO it looks the best of those.
Knights cross of the House of Hohenzollern with swords:
Pour le mérite
Military merit order of Bavaria, 4th class with swords:
Order of the crown with star (I have no image with the swords present):
Knights cross of the Order of the red eagle with swords and crown: