Hi ebonham,
I think I have a great solution to this fun problem. I tried to snake the filling of those servers without success. Then after doing your problem by hand many times it came to me. You need to give the next largest school to the server with the least number on it already. I used a little table in yellow to do a CountIf formula showing how many people were on a server down to any point in the rows. A third column shows how close to perfect the sort is.
You need to sort Column B from Large to Small and then run the code. The code clears Column C and starts down the column assigning each School number to servers. It will add the next (largest) to the server with the least number of people. Problem solved!!??

Server Distribution Fill the Least Server next.xlsm
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