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Generally, you’ll want to prune back the trunk by 1 to 2 feet each year to promote bushy growth. Doing so concentrates vegetative buds closer to the bottom of the tree, where you can easily harvest fruit. For side shoots that are a year old, leave at least six leaves. 

Never remove more than 30% of a tree’s foliage during pruning—even if your tree is really overgrown. Removing this much foliage at a time could kill your tree.

The ideal time to prune a tree depends on the type of tree. Typically, late winter or early spring is a good time to prune but isn't always the case for "towering trees." It's best to trim when trees are dormant and before blooms appear but can vary depending on the tree type. It's always best to research the type of tree or ask a professional tree trimmer to determine when is the perfect time to prune your tree.

Consumers typically do not need to worry about the cost of tree insurance, as professional tree service companies pay for their own coverage. For a tree service business, an average U.S. policy covering about $1 million in general liability costs roughly $40 a month or $500 a year. More extensive policies, providing between $500,000 to $2 million in coverage, can cost between $3,000 and $6,000 annually, depending on the company's size and scope of work. Tree service professionals should speak with an insurance company to determine the right plan for their business.

Yes, tree roots can regenerate after they’re pruned or cut. In fact, trimming can stimulate new growth, especially in healthy trees. The tree’s roots can still grow back even after a tree is cut down, (and learning how to get rid of regrowing tree roots is a separate feat). Still, if you don’t wish to harm a tree, pruning the roots should be done with extreme care, and ideally by a professional.