I don't collect paper but I do not see any issues with these items.
Live to ride -- Ride to live
I was addicted to the "Hokey-Pokey" but I've turned
My greatest fear is that one day I will die and my wife will sell my guns for what I told her I paid for them
"Don't tell me these are investments if you never intend to sell anything" (Quote: Wife)
They all look ok but are you aware the Verdienstkreuz fuer Kriegshilfe looks like it was awarded to another member of the family? Looks like Goerg Glauner whereas the rest appears to be for Karl Glauner.
Can you read German? It's mostly to do with his uni studies - being accepted to the Tuebingen Uni, Mittags and Abendsfreitisch are perhaps free meals.
The Feldpost letter is adressed to Unteroffizier(?) Carl Glauner in April 1917 while he was in a field hospital whereas the iron cross certificate is to Gefreiter Glauner and dated later in the year. Perhaps demoted for whatever reason and perhaps he received the iron cross for whatever he did when wounded.
I could be incorrect about the words I've translated but all in all a nice group to Georg and Karl Glauner.
The collection consists of the following items. I hope it helps with your decision.
(1) The Merit Cross For War Aid (Verdienstskreuz für Kriegshilfe) awarded to Oberbahnassistent Georg Glauner in Leberau (today known as Lièpvre in Alsace. This region belonged after the Franco-Prussian War 1870/71 to the German Empire.)
Note: I am not sure how to properly translate the title "Oberbahnassistent". Assistant at elevated railway / monorail?
(2-3) Feldpost Letter from 17 April, 1917 addressed to Unteroffizier (sergeant) Karl Glauner, who was at the time at infantry hospital in Braunschweig. The content is as follows:
"Sonntag, den 15. April 1917. Lieber Karl, du bist jetzt Offz.-?. Die Bescheinigung wird dir in den nächsten Tagen zugehen. Deine förmliche Ernennung lag noch nicht vor. Der Oberleutnant war, als ich ihm die Sache vortrug, sofort bereit, dir den Schein auszufüllen, für einen so tüchtigen Kerl, den er bedauert nicht mehr bei sich zu haben. Bitte bald um ein Bäldchen(?) als Flieger und Feldwebel. Glück auf! Dein Heinz."
"Sunday, 15 April, 1917. Dear Karl, you are Offz.-? (perhaps officer candidate?) now. The confirmation will be delivered to you in the next few days. Your formal appointment has not been submitted yet. When I introduced your case, the senior lieutenant (Oberleutnant) was at once ready to fill out the confirmation for such a capable fellow, whom he regrets no longer to have at hand. I ask you for a quick message(?) as a flier and Feldwebel. Good luck! Yours Heinz."
(4-5) Request for discount on student return tickets. Issued to Karl Glauner, born on 20 Juli 1897, in order to visit on Sundays and holidays his parents in Sülz. He was a regular student at the University of Tübingen from 1 June to 15 August 1921.
(6) Confirmation that Karl Glauner is accepted to study at the University of Tübingen, 19 April 1920.
(7) Confirmation that the student Karl Glauner is allowed to have a free lunch and dinner at the university cafeteria from 2 April to 3 April 1921.
(8) Award certificate to the Iron Cross Second Class to private first class Glauner. Probably a sibling of Karl Glauner.
Oberbahnassistent just means bahnassistent first class. Nothing to do with which type of railway.
Like Jager and OberJager Forstmeister and Oberforstmeister.