Bill should get long-term disability and carry it his entire life, but he shouldn't buy disability insurance pre-tax.
ANSWER: Yes, you should have long-term disability and carry it your entire life. You should carry all you can get – which is usually 60% - 70% of your income. Don’t buy disability insurance pre-tax. If you get it through work, pre-tax, then your disability income is taxable, and you don’t want that.