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Ideally, you should wait to prune until trees have gone dormant in late fall to early winter. The worst times to prune trees are early fall and late summer, as pruning them so close to dormancy makes it difficult for the tree recover before it goes dormant for the season.

The best time to prune Japanese flowering cherry trees depends on where you live and the type of flowering cherry tree. Some trees benefit from being pruned toward the end of winter or early spring, after the last freeze. Meanwhile, other trees do well after blooming, in late spring or early summer. Avoid pruning your flowering cherry tree in the early winter, as this encourages open wounds that can lead to infections or infestations. 

A tree can grow back from its stump, but full regrowth is unlikely (especially for more stubborn conifer trees). Instead, trees are more likely to send up a number of shoots from the dead stump, which will try to develop into primary stems over time. In other words, it will start to look increasingly bushy. The goal of killing and drying out a tree stump is to prevent that from happening, as well as make the stump easier to completely remove.

Most experts recommend removing a tree that has sustained more than 25% loss in the limbs, trunk, or circumference of the bark. Doing an initial trimming of damaged and dangling branches, but then waiting a few days of monitoring to decide how much more you might need to cut can help you better assess the total damage to the tree. However, consulting a tree maintenance pro to make this determination the best course of action before removing a tree.