Absolutely positively get a new roof done if the service life of the shingles is past.
I actually re-did mine 1 year before I FIREd because I knew it would be very difficult for me to afford such an expense postFIRE. There were allegedly 3 years left on the service life of the shingles. However, I had already seen that there was some damage done by shovelers I had to hire one very
snowy winter. They got a little carried away with cleaning off the snow.
So I replaced it sooner than the service life of the shingles, just to be on the safe side of the effects of that damage.