So the first thing I did was use the transpose tool to bring the item number name into their own column and grouped by transaction number, before using a select tool to rename a couple of the columns. The filter tool was used to remove any null entries in the columns and the sort tool was used to sort the Item column into alphabetical order.
Next I used a formula to assign a value to each type of item, my thinking being to calculate the total of each transaction and each unique number would be an unique combination. After assigning the values and changing the data type to double it was a case of using a summarize tool to calculate the total of each transaction and then another summarize tool to count the amount of distinct numbers.
The final select tool was just used to rename the column to match that of the given output.