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The best time to transplant a tree is when it is dormant. For many trees, this means either in the fall after the leaves have dropped (around October or November) or in early spring before new growth begins (around March). The ideal timing can depend on the type of tree. Deciduous trees do well when moved in early spring or fall, while evergreens are best transplanted in early spring or late summer. For example, pine trees are best moved in early fall, but maples prefer late fall. Avoid transplanting in winter, as the frozen or hard, cold soil poses a significant risk to the roots and prevents the tree from acclimating properly.

Carefully pruning small roots no thicker than three inches in diameter won’t harm the tree. However, cutting larger roots may impact the tree's stability and nutrient absorption. It's advisable to consult an arborist or tree care professional to evaluate the root's size, the tree's health, and the potential impact of cutting. Proper tree pruning techniques and timing can minimize damage, but larger root removal may necessitate expert guidance to avoid compromising the tree's overall health and stability.

It depends. Smaller, younger trees take longer to mature, but they're more resilient, their roots don't get as damaged during transplanting, and they recover faster. Plus, they're much more affordable to plant, and it's possible to DIY the planting. 

On the other hand, mature trees produce fruit faster and provide more shade and privacy immediately. Ideally, a small or medium tree is the better choice if you can wait a few years for it to mature. But if you need immediate maturity, a larger tree is the only option.

You can shape a cherry tree by trimming vertical branches, dense branches, and intersecting branches. Your personal aesthetic comes into play, as well. If you want to simply thin and shape the tree, you can get away with trimming the aforementioned parts of your cherry tree. If you want to shorten branches, however, consider thinning cuts, which alter the length of the branches while encouraging light penetration, new buds and shoots, and a structurally-sound shape.