After talking with the roofer...

I'm going to think about it for a couple of days.

The damage to the roof was not as extensive as it appeared mostly because the roofer noticed that my house had two layers of shingles and the top layer of shingles were stapled there. This made it easy for the wind to remove the top layer of shingles. The roofer also noticed the lack of hail damage to the roof which is what most insurance adjusters look for before making that decision to issue a check.

I discussed three possible jobs with the contractor:

1. Performing simple repairs to areas of the roof that were affected by weather.
2. Replacing the downspout drains from the guttering with drains that are wider in diameter. This gives debris like leaves and sticks a better opportunity to drain through as it rains. The roofer also offered estimates for installing gutter screens (not helmets).
3. Installing a new roof altogether. I'm seriously considering this idea because I can easily see myself living in this house for another 15 years.

Decisions, decisions. I need a beer.