I use Chutes 'N Ladders (https://www.yelp.com/biz/chutes-n-ladders-portland) on my house in Portland, Jeff and his wife are a nice small family company. They have an twice a year visit deal where they clean gutters and roof, do any minor repairs, and call me with a quick rundown of the condition of the roof. They are reasonably priced, nice to deal with, and have been mostly consistent. They work with me via phone or email and it's easy. They have been nice about calling me for payment or renewals when I forget to pay the bill or otherwise am disorganized.
The only screw up was that they missed an appointment before the torrential rains in November a couple years ago - that was crappy and my basement got a bit wet. They explained that they had to drop everything because the wife went into labor and had their kid a couple months early. Gotta cut them some slack for that.
another Handsome Boy graduate
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