I have a 750GB HDD. Speaking visually (looking at Disk Utility) I had a 250GB Mac Journaled partition on the top, and a 500GB Mac Journaled partition on the bottom. The 250GB partition is now free space, now how do I expand the 500GB partition upwards?

I have a 750GB HDD. Speaking visually (looking at Disk Utility) I had a 250GB Mac Journaled partition on the top, and a 500GB Mac Journaled partition on the bottom.
The 250GB partition has been deleted and is now free space.
Now how do I expand the 500GB partition "upwards" when the GUI only gives me a resizing handle on the bottom right corner in Disk Utility?
I am comfortable with Terminal if there is a non-destructive CLI way to do this, since the Disk Utility GUI seems to have failed here...

OK.
You will need to check out a third-party utility.  The diskutil CLI utility cannot non-destructively change the start of a partition map, only the end (which is why you only get the draggable handle in the GUI at the bottom of each partition...same idea).
To be honest, I'm not even sure how well third-party tools will do at this either.  Changing the start of a partition is non-trivial, be cause of the partition map files, b-trees and so on which have to be moved.  iPartition is well regarded, but also not free.
And regardless of what tool you use, you will want a backup of your data (assuming that it's data you want to keep, or you wouldn't care about non-destructive repartitioning).  Which might mean that just getting a new HDD , copying the data and then repartitioning the current one and having an extra HDD because of it may be the simplest and safest solution anyway...

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