There's this book I really enjoy, "From Latin to Spanish" by Paul Lloyd, that goes at length on the phonological and syntactical evolution of spanish and, damn, spanish really did take quite the funky path in the evolution of its phoneme system while portuguese remained conservative in plenty of its inventory. It's really fun to compare them and see where they diverged and how some phenomena are really quite distinctly romance, like palatalization due to a yod.
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