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SUBMIT YOUR IDEANice challenge, find my solution below.
I used the Tile tool to create 5 manual buckets and then a Formula tool to prefix the letter "R" to the generated [Tile_Num] field. I then joined the two tables on this newly created "Region" field and the pre-existing "Region" field in the other dataset and used a Summarize tool to get the required results.
My first intermediate and I think my solution is pretty long-winded!
My first instinct was that we really need a tool that can handle flexible join conditions other than A=B. Then I decided to use the Append function to essentially do a cross product between the range data and the customer file. I was able to get this to work, but after reading some of the posts I realized this approach was very limited and would not scale well if we had a large set of regions. My final approach used generate rows and then a standard join, giving a much more scalable approach.