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Although it’s possible, heavy machinery like a crane is necessary for removing an entire tree stump and all. This procedure is extremely costly, time-consuming, and usually unnecessary, as there are plenty of convenient and affordable stump removal options. 

Your best bet, if you want to be sure to remove a tree and its stump efficiently, is to speak with a professional. They’ll be able to walk you through the entire process.

Ideally, you should wait to prune until trees have gone dormant in late fall to early winter. The worst times to prune trees are early fall and late summer, as pruning them so close to dormancy makes it difficult for the tree recover before it goes dormant for the season.

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.

Any cutting of tree roots can hurt or kill a tree, which is why it's recommended you don’t do it unless the roots are damaging or invasive on a nearby structure like your home. You should never cut more than 15 percent of above-ground tree roots at one time. If you have any questions about cutting tree roots, contact your local arborist.