I don't think the press "so reflexively call everything Trump does a tragic failure " as stated by the link in the OP (emphasis added). In fact, the press I saw from Texas and Florida was largely positive, and I've certainly praised Trump's response to both of those natural disasters as well. Similarly, the press that I saw on Trump's remarks yesterday was largely positive also (as well as my comments on it). Regardless, I don't recall seeing any press on those three issues which called (or implied) they were "tragic failures". I think pundits dilute their message by providing such sweeping generalizations that simply aren't true (at IMO). Certainly the press is liberal. Certainly the press holds Trump to a different standard than Obama or that of other Democratic Presidents, but "everything" "tragic failures"? Come on.
Puerto Rico had several challenges unique from Texas and Florida: the nature of the geographically, the lack of infrastructure, the amount of devastation. Couple all of that with the fact that this was the third major national disaster in a short period of time that FEMA had to respond to, it was absolutely an incredibly challenging situation. Regardless, while people are still suffering, Trump and his Administration do themselves no favors, IMO, by proclaiming it's a "good news story", counterpunching local officials who are right in the middle of the fight for survival, and giving themselves an "A+". The time for patting themselves on the back is once things are stable throughout the island not while 1/3 of the ports are NOT operational, 1/3 of supermarkets are NOT open, 2/3 of the ATMs are NOT working, and 60% of telecommuications services are NOT restored. Another self-inflicted wound IMO.
