We're definitely getting other estimates. The gutters are also pretty much a need, not a want. Our gutters now don't work properly, despite that my DH has spent countless hours messing with them. The $17k estimate doesn't actually include the price of gutters. He was going to "gift" them to us if we decide to use his business, as long as we let him know within the next few weeks. He also mentioned the fact that he can knock a few hundred or so off if let him advertise in our yard and leave him a yelp review, which I don't mind either of those if we decide to go with him.
@imbatman I know you said you have family in the roofing business, do you know anything about Owens Corning? Whether or not they are good or not? This is the brand that he works exclusively with, but since I know nothing about roofing I have no idea if they're decent or not.