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A tree can grow back from its stump, but full regrowth is unlikely (especially for more stubborn conifer trees). Instead, trees are more likely to send up a number of shoots from the dead stump, which will try to develop into primary stems over time. In other words, it will start to look increasingly bushy. The goal of killing and drying out a tree stump is to prevent that from happening, as well as make the stump easier to completely remove.

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 wondering whether you can plant a tree where the stump was removed, know that the soil conditions won’t be ideal, so you should avoid it. The soil beneath the previous tree will likely be depleted of nutrients, plus there may be roots left behind that will seriously hinder the growth of a new tree. Also, if you use salt or other chemical solutions to kill the stump, these can linger in the soil for months or even years and prevent healthy growth. It’s best to choose a different spot that’s at least three feet away for a new tree, or wait at least a year and thoroughly amend the soil before you plant.

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.