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It is possible to plant a tree over a ground stump if it was ground very deeply. However, it is typically best to plant elsewhere so your new tree has room to establish a strong, healthy root system. If you want to plant a tree in the same spot where you currently have a stump, you may want to consider other options, such as stump removal.

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.

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.

It’s usually best to buy plants from a local greenhouse or nursery yourself, but landscapers are also a reliable option. First, you can choose exactly what plants you want based on their appearance rather than relying on your landscaper to choose. Additionally, while it’s more time-consuming to go buy the plants yourself, you’ll often save money because landscapers charge for delivery and may upcharge the plants. You can also speak to a professional at a nursery to ensure you understand how to care for your plants and get the most long-term value.