Multiple pickings are usually required of all cultivars I grow and is a well understood aspect of commercial growing where trees are rated by the span of time between first and last ripening fruit. For commercial growers the shorter the span the better because it makes harvesting more economical but for home growers the opposite trait is often desirable, especially if fresh eating off the tree is your primary pleasure. I recommend that home growers should study the catalogues of nurseries for commercial growers like Adams County where this information is often included.
When you want to pick your fruit will often be determined by how you plan to use it. A firm peach jars better and a slightly green apple stores longer as does a hard pear. Culinary use often benefits from less than complete ripeness of fruit because riper fruit is juicier.