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Yes, it’s possible to overwater a newly-planted tree. Daily watering is great for the first few weeks, but it’s important not to go overboard. Excessive watering can lead to various problems, including root rot, fungal diseases, and a lack of root development.

You should not trim an oak tree in the summer. Oak trees are especially susceptible to disease, and open tree wounds are an invitation for beetles that carry tree-killing fungus. If there’s no risk that the oak tree will do damage to your property or hurt someone, it’s best to save the trimming for fall or winter. If you can, seal the wound with latex to prevent fungus from getting inside.

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.

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.