It costs money to upgrade and stabilize the power grid. It costs money to stay ahead of the failure curve.
The current infrastructure sucks mainly because it's unpredictable and takes too much effort to synchronize disconnected sections of the grid before connecting them. You can't just "route around" a dead transmission line if there are generator stations active on both sides of the break. You must wait for the two sides to synchronize in phase before connecting them, which can take several seconds to a minute. If you don't, you'll cause even more breakers to trip.
None of this would matter if we switched distribution to HVDC. We have the technology, but again, the cost to convert everything to employ DC-DC switching converters is prohibitive. The biggest upside to switching everything to DC (all the way to the end-user) is that you could add standby capacity by simply connecting batteries to your mains circuit between the main breaker and load panel. The more people in a neighborhood using batteries to buffer their power source, more aggregate protection the neighborhood has against blackouts.