It may depend on your particular state but, e.g., in Wisconsin money for pain and suffering is not taxable income.
Settlements that are paid for a physical injury are not taxed. The settlement that you receive for a personal injury claim such as slip and fall cover lost wages, medical appointments, and pain and suffering. These settlements are made so that a person can feel "whole" again.
A settlement is usually split into two parts, recovery of damages sustained, and pain/suffering (putative). For recovery of costs, the settlement is not taxed. For pain/suffering it is taxed.
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The "payout" is commensurate to the amount of pain and suffering you actually experienced. Stress is not recoverable.
Insurance company is required to pay for actual damages. This means putting you back to where you were before the accident, not hitting the lottery to get something for nothing. There is no pain and suffering amounts.
Worker Comp does not pay for pain and suffering. They only pay for actual medical expenses incurred due to the workplace incurred injury.
Your own underinsured / uninsured (UM) policy is designed to pay to you, the policy holder, if an uninsured or underinsured person is at fault and causes injury to you but that's only if the other driver was at fault and you were injured. If you injured yourself in the accident (you were at fault), then your insurance will NOT pay pain and suffering awards. If they did, there would be many, many, many people who would stage accidents to 'injure' themselves and then claim pain and suffering awards.
Working under the table - he paid you but he didn't with-hold taxes. He probably didn't pay workman's comp insurance. You can try to sue him - but, you'll have to pay the taxes. You might get in more trouble than its worth.
You can sue your insurance company for a higher amount but there is no guarantee that you will win. You will need to have proof and be convincing that you deserve more money for the pain and suffering.
Yes. The attorney works for you and your interests such as personal property, medical expenses, lost wages and settlements for pain and suffering. The insurance company, either yours or theirs, works for the insurance company and will give you only the minimum required by law based on a scale which computes market value of personal property, exact costs of medical expenses, exact lost wages from time off of work due to injury and as close to zero that they can legally come to in settling pain and suffering compensation.
As little as possible while taking as long as possible. Hire a lawyer.