Homer said that you should Hit if you're strong or Swing if you're quick.
However, I think there's another very important determinant which is rarely mentioned: Hinging. Some players find it very easy to perform the Full Roll feel of Horizontal Hinging, while some players find the No Roll feel of Angled Hinging more comfortable. This has huge implications when choosing between Hitting and Swinging. Essentially, they have different Rhythm -- and that's one of the harder things to teach. If one student finds Full Roll easy to do then he/she probably is already Drag Loading and using Centrifugal Force. The 'Hinging Test' should always be performed when deciding.
Regarding comments that Swinging requires better timing, I disagree. Hitters need to apply their precious Right Arm Thrust at a very precise moment to overcome their inherent problems in Release Deceleration. For Swinging, CF takes care of the squaring of Clubface, CF ensures the Clubshaft stays On Plane, and CF allows the Clubhead to fly into its correct orbit. However, Swingers need to perform Startup and Release Swivels which may or may not need to be consiously learnt. The Start up Swivel should occur automatically if you're preparing to Drag Load. Points and counterpoints...
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