The safest way to cut down a tree is to make sure you’re completely prepared and have done all the necessary safety checks, including double-checking your equipment is in good working order, you have plenty of clearance to fell the tree, you’re wearing all the safety gear, and you have a partner to help you (who should also be wearing safety gear). 

The best time to cut down a tree is during its dormant season, typically in winter or early spring, after all the leaves have fallen. Removing a tree during this period is advantageous for several reasons. Frozen ground helps secure the tree stump, protects the surrounding landscape from damage, and reduces the risk of the tree falling in an unintended direction. With the leaves gone, there is less risk of the tree's foliage getting tangled with other trees. Additionally, since this is often a slower season for tree services, you may be able to hire a professional at a lower rate. This dormant period is also the best time for tree trimming.

You may wonder whether tree removal is tax deductible: Tree removal is not tax-deductible for homeowners unless it's related to a federally declared disaster. In that case, the cost may qualify as a casualty loss. However, if you own a commercial property, like a rental home, tree removal could be deductible if it's necessary for safety, maintenance, or part of a larger capital improvement project, and you must hire a professional tree removal service and keep documentation. Always consult a tax professional beforehand to see if you qualify.

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.