Many home owners just like many car owners pay high maintenance costs because they don't understand "preventive maintenance". I have a neighbor who is like that.
We have a lot of large maple trees in the neighborhood so I use an attachment on my leaf blower to clean out the gutters several times a year. The neighbor has not cleaned his gutters since he moved in 3 years ago. As a result all the leaves, etc. have collected in his gutters and turned to compost to the point that trees were sprouting in the gutter.
During the last rain storm we had part of his gutter fell down so he got someone to repair it. Turns out that the reason the gutter fell (besides the weight of the junk in it) was that the water overflowing the gutter had rotted out all the fascia boards and even some of the actual roof boards.
Now he has to replace the gutter and the fascia and at least part of the roof all around the house. A couple hours a year of some preventative maintenance would have saved him the $10K he has been quoted to repair the damage.