Good job! I've never done roof work, but have done concrete flat work and quickly learned it was not what I wanted to do for a living.
Similar to you, some years ago I had a rental far from where I lived. It was an attached, zero lot line, duplex style house. The owner of the other side worked to get a few quotes for a new roof over the whole building. The first quote was $9000 ($4,500 each), second was $12,000 and the third $24,000. The first quote was from a contractor that lived in the neighborhood. He crawled all over the roof taking measurements and provided a detailed description of what he would do for that price. The second contractor also crawled across the roof for measurements and was competitive with the services offered. The third was from a large contractor that advertised heavily in all media formats. The estimator didn't even get out of the pickup. He parked in the driveway, rolled down the window, and stated a price. We obviously went with the first contractor and the work was top notch.