I had a leak near the roof edge, and sagging eavestroughs that needed to be replaced. Kevin suggested fixing the eavestroughs first as they needed to be re-done and might fix the leak, then consider re-shingling later on or next year as they were starting to curl. The leak ended up being not just the eavestroughs, so I also had the roof re-finished right afterward -- all done within a week.
After getting the roof work done, and a short wait for another rainy day, there was no leak or dripping gutters in a moderate rain.
Kevin was happy to explain what he planned on doing, and why: remove the downspout draining into the sewer, trim the over-long roof deck hanging over the edge, re-do some vent flashing, add ice barrier, re-do the attic ventilation, use a slightly heftier shingle than the previously installed 3-tab shingles, and fix a bathroom vent with a torn duct pipe.
I was happy with the price, and didn't have to schedule the work months away into the future. Eavestroughs were done by a small team over the course of two days, and the roof was done by a larger team in less than a day. Our yard was cleaned up right after both the eavestroughs and the roof. Between tarps covering the area around the house, and the magnet sweeper, we haven't been finding nails.