After a bad hailstorm or a few years of heavy snow, it's worth getting a roofer up there to take a look. You might not see the damage from the ground. Cracked shingles, lifted flashing, or compromised valleys will leak into your attic for months before you notice water on your ceiling.
A legit roofer gives you a written inspection report, shows you photos of the issues, and explains what needs immediate attention vs. what can wait. They'll also help you navigate an insurance claim if the damage qualifies. Bad roofers show up door-to-door after every big storm, rush you into signing, and disappear after the check clears.
Roof replacements in the DMV run $8,000-$20,000 for most homes depending on size and material. Get three quotes, check they're licensed and insured in your state, and look them up on the Maryland Home Improvement Commission (MHIC) database. If they're not in it, don't hire them.