Details of aerial images showing Irma's destruction in Key West
Some of the most impressive damage close-ups came from "before and after" shots that had no "before" equivalent (because the original aerials weren't as high of a resolution). I've included those here as well, with commentary.
The worst damage (that I saw on these images) was in the "Avenues" area of Big Pine Key. As the storm approached, they took the most direct hit from the strongest eyewall winds and storm surge, with almost no barriers, as illustrated here:

This is what it looked like: nearly complete destruction for the first several rows of houses; debris piled up in the canals, RVs tipped over, random cars and boats in yards.

Elsewhere, this is a close-up of an RV park in Marathon, Florida. Although other parks were evacuated, for whatever reason, the Sunset Key Mobile Home Park was not one of them. This was a bad idea. At least half of the trailers are overturned and many are damaged. Random boats and seaweed in the park indicate that the entire area was under water during the storm surge.

Next is a look at Highway 1, the main drag down the Keys. Here you can see that the entire highway was overwashed with rocks and sand. Most of the highway had been cleared in the days before these overheads were taken, but this was an exception. If you look closely, you can see the bulldozers working on it.

Below are shown piles of metal pipes: what is left of one of the hangars at Key West Airport. Normally planes are parked in this area.

At the Bahai Honda State Park, a large building that I believe was part of the park was re-located across the sound and crushed next to Highway 1. Old Highway 1 also ran north of the structures in the sand at the bottom of the image, but it was broken up and covered by sand during Hurricane Irma.

An RV park on Big Pine Key saw all its homes floated into a pile, with some in the bay:

On Cook Island, a remote house had half of its roof torn off and deposited two houses away.

Down the road (which isn't much of a road anymore, as its covered with downed trees), one house was floated a city block away from its brethren.

And at the point of Cook Island, a home was destroyed after it was washed back a city block or so.

At Long Beach on Big Pine Key, the beach had washed over the road in several places, even shifting a good portion of it on a 25-degree angle. One of the houses was washed across the road and deposited in pieces in the bay.

Watson Road on Big Pine Key was overwashed with debris near the bridge, and almost every home on that part of the island was heavily damaged.

Again, boats were left stranded everywhere, even in the woods.

Another RV park destroyed.

Even when the houses survived, the docks did not.

SIDENOTE: I also looked at the aerials up the coast to Tampa, Florida but damage was hard to find from the air. You have to look for weaker structures like these greenhouses in Tampa.

Also, sub-standard housing communities like this, where almost all the buildings were damaged.

An exception was one of the most exposed, and southernmost islands before the Everglades and Key West: Goodland, Florida. There you saw significant structural damage, RVs on their side, and debris everywhere.

