You'll have an advantage when the squirrel is cleanly killed without excessive damage and you don't wait all day to skin. I always prefer the "stepping on the base of the tail" method on a good squirrel. You need a proper smallish knife, make sure you cut the tail bone at the base joint without going through the hide on the other side, make sure you cleanly nick the hide to go around each side to leave the pants, and make sure you firmly step on the base of the tail with the ball of your foot against a solid object. The hide comes off like a sock. It doesn't take too many squirrel under the belt before you'll get it down well enough to clean a mess of squirrel in short order.
Squirrel that are poorly shot with excessive damage and have sat around all day before skinning may prove tricky and could tear in half. You may need to extend your nicks further around by partially skinning the hide around the back and each side so the base of the tail has a flap which goes around the waist a bit. This will make the pull to start the pants a bit easier which may reduce the chance you tear the squirrel into pieces. If the squirrel is too shot up, you probably need to switch gears and use the method where you split the hide in the center and pull out from the middle with your hands in opposite directions.
The more squirrel you clean and cook, the more you strive to take them cleanly with minimal damage. Eventually you find the right combination and a difficult squirrel becomes the exception and not the rule.
Best