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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.

Multiple rules of thumb exist when discussing tree planting. When planting a tree, the best rule of thumb is to provide it with everything it needs to survive and thrive in its new environment. That may mean learning about the type of tree you're planting and studying the best methods of taking care of it before purchasing and planting. 

Yes, such as sod installation and erosion control for comprehensive site improvement.

Late August, September, and mid-October are the ideal months for planting a young tree. However, the best time to plant a tree ultimately depends on when the weather transitions to fall-like conditions and eventually winter frost. As long as the hottest days of summer have passed and the ground hasn’t frozen yet, you can still successfully plant trees.