In my area, we allowed trees to be trimmed near wires and poles. We neer lost power. In the Tree Hugger areas, power was out for the longest times.
Up here, so far, the Darwin Award wannabes don't get to tell the utilities if they get to trim on their right-of-way. Long private lines on rural property, I'd say that you are pretty much on your own wherever you are - as it should be.
Cities have concentrated services, but that only works quickly up to a certain level of damage. Out in the middle of nowhere, for a first-pass work-around, you could run a dozer down many rural roads and just push debris to the side for the time being, and open a road fairly quickly. In many city environments there isn't space to do that temporarily on a road, and cleaning up line damage in residential areas with mature tree canopies can be really time consuming - you are dealing with many fallen trees jammed in amongst relatively (compared to rural spaces) tightly packed houses - hard for heavy equipment to move fast.
I don't personally panic if the power is out for a couple of hours. I view the medium term limit as about 8 hours, with Winter obviously being the critical factor - beyond that in most households you better start planning for draining pipes in the dead of our Winter if you have no grid-independent source of heat.....
I remember a cbc news item on a multi-day power outage in Toronto. The news crew was walking down the road near High Park (old, now expensive, large homes, amongst old urban tree canopy) and found one guy helping out half a dozen neighbours. It took a guy from the Yukon visiting his in-laws to go out and buy a Honda EU2000, some wire and plugs, and wire up those half a dozen gas furnaces - he just kept rotating the little EU from house to house, keeping them heated. A little Honda suitcase gen was perfect for that application - plenty of power to keep the heat running short-term, quiet for 24hour operation (and not attracting attention), and easy for one person to move.....
On topic, that outage scenario is a good example of the utility of being able to split up 2 generators when desired....
When I think of disaster recovery, skilled people, equipment, and fuel are some of the first things I think of. The limiting factor I see coming into play more often locally (though, I'm sure it's wider spread than that...) is financial. You may have men, equipment, and fuel in place, but more often once they hit 44 hours (or whatever your regional limit is....) , the CFO dictates "Down Tools, until the next pay cycle starts.....". You need to know somebody inside that environment to hear that story; obviously they don't release it publicly....
If you live in the middle-of-nowhere, last on a long rural power line, it's fairly intuitive to expect being out for a while after a major event. In contrast, I've seen enough major urban events in the last 20 years or so to know that living in a high-density urban area does not guarantee fast grid recovery. Many cities are under much more financial pressure than they were 50, or even 20 years ago.....
Rgds, D.