Although I don’t know the actual evolutionary path annuals and perennials have taken it is easy to see how each could evolve into the other. I’m sure some annuals follow a very strict timing in their life cycle, dying after their seeds mature no matter what the growing conditions are, but others such as tomatoes can stay alive for many years as long as the conditions remain appropriate. Given enough time in intermediate conditions there are many ways species could adapt. Perennials with the shortest time to seed will tend to survive worsening winter conditions that might kill the whole plant, and annuals that can sacrifice their leaves and maintain their root systems during winter can survive shorter growing seasons. That kind of adaptation by annuals may have led to the evolution of biennial plants which follow a two year or two season life cycle, usually requiring a period of winter dormancy followed by a second season to flower and seed.
Most of the flowers that we think of as “spring flowers”, like daffodils, tulips, hyacinths, and lilies, are bulb flowers. The bulb is the part that (usually) survives, and from which the rest of the plant regrows.
Not just survives but needs the winter. Many of the bulbs, that we grow in the south, need to spend weeks in the fridge to get their chill hours.
Animals kind of do that. Anybody with a pet cat or dog knows about this each spring, when they begin shedding. (And go on, and on, and on…) Many livestock species do this too; they shed much of their coat in the spring.