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I’ve noticed a pattern where the simplest solution DOES accomplish the goal, but isn’t what a user might consider the “shortest path”. How do you count a workaround where it technically can accomplish the end result, but requires a minor annoyance? What about a major annoyance?

What about a process so painful nobody has even thought of it?

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It's nigh impossible to solve any complex issue with the "simplest solution" from the first try. This means that when you're faced with a complex issue you will postpone the fix because it's not the simplest.

And you never know if it can be done in an even simpler fashion later.

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