Will an insurance company insure a home with 27 year old roof?

Answer 1

Some will yes, but they may require you agree to an exclusion of the roof from policy coverage as it has already exceeded it's life expectancy. Once the roof has exceeded it's life expectancy, it is considered to have zero value. You can't really insure zero.

Answer 2

Some will, some won't. They might insure the home, but not the roof.