Might be because the grid has aged right along with you. The electrical power structure is still a private enterprise, with the desire for profit to match. They're not going to replace anything until they absolutely have to.
Roger
Yep, I think mostly that is what it is. An aging electrical grid. We do have outages, mainly because of where we live. Lots of right of ways lined with trees. Our power company does do a good job at restoring power after a wind storm knocks power out, and I'm very thankful for the pretty consistent power we do have. I have noticed that the power company wants reliability, and stives to obtain it. Could they replace all poles, transformers, lines, etc.. Yes they could, but the cost would be great which is transferred to the consumers. One good thing about a power outage once in awhile is that you run your generator, Its not good to leave a generator sit for long periods of times without making power.