I probably have the most obsession about avoiding damage in my area. I can count the incidents on one hand worth noting from the last 6 years:
window, metal roof, wooden fence, bench, ruts.
I cut and tossed an over-grown cherry tree next to a summer home; last limb flipped over and bounced back, putting the 3 in. butt end through a sliding window.$600, and the owners replaced all the windows a year later (they were old metal frame ones, and I had to have the replacement custom made so it would match).
Did several take-downs and pruned a big fir adjacent to a log home and garage, both roofed with aluminum roofing made to look like tile and painted black. This was a while back, and I was still learning rigging. When taking tops out of the oak removal, I miss-judged the drop on two 20-30 foot tops and the tips brushed the roof; didn't think anything of it at thee time. Almost 2 years later, the owners called and accused me of denting their roof. I checked it out, and sure enough, there were around 20 small dents in a wide row leading down the roof right to the stump. I happened to have taken a "before" photo of the oak, and no dents. $1,480, only one company supplies and installs this stuff, located 4 hrs away.
I had my good climber take down a large beetle-kill pine. All went well until the top was rigged down; because he had used his favorite rigging scrap (mistake one) for the block instead of my new heavy rigging, when the haul rope caught around the block (mistake two) the scrap broke, and a thirty ft. top flattened around 20 ft. of wooden fence. Of course it was made of 5 rungs of 40 yr. old clear-fir 1 by 10 -- but I cheated, and used cheaper clear cedar to replace the wood. Around $500, if I paid myself $25 an hr.
I put my low-skill climber (since fired) in a modest sized-birch take down while I pruned a large oak nearby. I looked over when he was making his last cut: a 6 ft. piece around 18 in. thick , with a rope tied to it and looped around another tree --- which was around 90 degrees off the lay. Before I could get his attention, he cut it and it fell on a custom-made bench, but did miss the sidewalk formed in concrete 3-D Escher designs (fish). He blamed the groundie who held on to the rope, causing it to swing a bit and miss the sidewalk, hitting the bench. Luckily, it was really sturdy, and I just had to replace some slats (clear cedar 2 x 4 s). I guess that made sense. Around $200 to fix the bench, if I had paid myself. I don't want to think about what the sidewalk would have cost to fix.
Ruts were made all over a lawn under a big plane tree, put there by a lift truck run by a sub. I had to fix the ruts before the college graduation on the same patch of grass a month later. I brought in soil, cut out the turf by hand with a shovel, and leveled around 5000 sq. ft. Only sub I ever fired -- he not only destroyed the lawn, but did a hack job pruning the plane and another large red oak. I also had told him to meet me on site so that I could oversee the work (and see his paperwork), and instead he came on the weekend without telling me. Turned out he didn't pay into workers comp because all his workers were "family"--- after I told the college that I would make sure that the company was fully insured. $500 at $25 per hr. (if I had paid myself). Same guy makes hat racks all over the area, and sends poorly or untrained climbers to do take-downs he can't get to with his lift truck.