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Yes, pruning makes trees stronger because it fosters proper growth, weight distribution, and balance of the crown. By increasing the structural integrity of the tree through pruning, it’s less likely to experience disease, pests, broken limbs, and storm damage. Pruning the right branches and limbs is key to improving a tree’s strength and balance.

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.

Ideally, you’ll have a good enough relationship with your neighbors that you can kindly mention this task in regular conversation. However, every neighbor (and neighborhood) is different. Your best bet will always be to ask directly and nicely, offering to contribute to the tree trimming efforts if you’d like. However, if you are bothered by the tree and your neighbor is unwilling to cut it, you can involve the help of the homeowners’ association or local authorities, if applicable.

If you’re taking down a tree that you don’t suspect is affected by disease or pests and it’s nowhere near your home or other structures, then calling in a tree company should work fine. However, anything more involved means an arborist is a better option. These pros have years of experience with tree removal and can safely take down trees located next to structures, and they have the tools, sanitization equipment, and experience to remove sick or dying trees without infecting nearby trees.