The Rules are not very complicated if you apply only the applicable rule to your situation and THEN determine if an addition Rule is needed.

Example: My ball is on a cart path. What does the Immovable Obstruction Rule (Rule 24) say?

It says I get a penalty free drop.

Dont worry about casual water, re-drop scenarios, or unplayable lies.

Find your nearest point of relief and drop the ball.

You are now done with Rule 24-2.

In the unlikely case that your dropped ball rolls into casual water (Rule 25), closer to the hole (Rule 20-2c), or into an unplayable lie (Rule 28), you may then invoke that Rule and proceed under its conditions.

If you use this step-by-step approach, the Rules covering every possible scenario can easily be applied one at a time.

Speciifically to your question:

1. You drop the ball ONCE.

Rule 20-2c covers seven situations in which a dropped ball rolls to a position where it MUST be re-dropped.

If the dropped ball has rolled and come to rest in one of these condiitions, you MUST re-drop the ball.

If the ball, when re-dropped still does not satisfy all seven conditions covered by Rule 20-2c, it MUST be placed on the spot where it first struck a part of the course when re-dropped.

This spot (where the ball first struck a part of the course when re-dropped) DOES satisfy the conditions of relief from the cart path.

This spot axiomatically satisfies the conditions of Rule 24-2 because Rule 20-2b stipulates that a ball when dropped must first strike a part of the course where the applicable Rule requires it to be dropped (in this case, Rule 24-2).

If the ball has not been dropped in accordance with Rule 20-2b, then Rule 20-6 allows you to lift the ball without penalty and proceed correctly.