Python's str.title() and string.capwords(str) methods have some flaws. Namely:
str = "my dog's bone/toy"
assert str.title() == "My Dog'S Bone/Toy"
assert string.capwords(str) == "My Dog's Bone/toy"
As you can see, str.title() doesn't quite format the string "Dog's" correctly - it instead opts to convert the "'s" to uppercase. This results in somewhat nonsensical strings.
string.capwords(str) is better about honoring the possessive case, but it has its own flaws. Firstly - it doesn't recognize words that occur after common punctuation like /, ( ), -, _, etc. This means that "bone/toy" will only be converted to "Bone/toy"
I've written my own answer to this problem, hopefully it helps anyone else who needs to capitalize the first letter of each word after punctuation without using title() or simply relying on capwords().
My solution first takes advantage of title() to solve most of the capitalization. It then uses a Regular Expression to look for an upper-cased letter preceded by a single quote mark that is in turn preceded by a lower-cased letter(this solves the issue of retaining contractions while matching single quotes within strings.)