Along the lines of making sure the quotes are all on the same things, ask about their assumptions. Full tear off (and haul away), or just put on top? Ice & water barrier? Any decking repairs needed? Gutters, flashing, etc? What kind of shingles: three tab, architectural?
What about a different kind of roofing? Metal roofs have become very popular in this area. When we needed to replace only a part of our home's roof (a single story ell) we did it ourselves with architectural shingles. We had planned to use the same when the rest needed replacement. By the time the garage needed a roof job, metal had begun to appear, and we decided to try it, hoping a longer lifespan would be a good trade off. DH did this one, too. Last year when we needed to finally do the main roof, we had an Amish crew install another metal roof for us. Bigger job, two stories, metal is slippery (DH found out the hard way on the garage) made it worth it for us to hire this job out.