Do I need to get on the roof to inspect it?

No. You can do a thorough inspection from the ground with binoculars and a sturdy ladder for gutters. Walk around the house and look for missing or curled shingles, granule loss, or sagging. For gutters, use a ladder on level ground and poke around with a trowel or stick. Check foundation cracks from the basement—small vertical ones are usually just settling.