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Cutting down a dead tree is always strongly advisable. Aside from being an eyesore, a dead tree can be extremely hazardous, especially when it’s near people or structures. Even if the tree isn’t near your home, it can still harbor pests and diseases that can potentially spread to nearby plants and homes.

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.

If you’re planning on keeping the tree, unless the roots are invasive, there’s no need to remove them, as doing so can cause damage to the tree. If the tree has been cut down and the stump and roots are left, grinding and removing the stump can cause root decay for some species. For other species, the stump and roots will need to be removed to prevent pests, disease, and possible tree regrowth.

If an arborist is certified by the International Society of Arboriculture (ISA), the highest level of certification available is ISA Board Certified Master Arborist. According to the ISA, this credential is reserved for arborists “who have reached the pinnacle of their profession.” Check your arborist’s credentials before hiring to confirm their level of training and expertise.