First of all... you can't compare capital expenditures over a decade (actually primarily the last five years or so) to the amount of income produced by them during that time. That's almost as nonsensical as buying a home and then comparing the amount of rent that you saved in the first five years. The asset is still there and still producing (and no... it isn't a big deal that individual wells have steeper depletion curves than traditional wells).
Second - the US consumes about 20 million barrels of oil per day. Before fracking knocked OPEC out of the driver's seat on oil prices...we were paying $120-$150/bbl - which means that during this period that they were losing the most money, they were saving consumers about twice that amount every single year. Even with prices back over $60/bbl, that's a savings of over four tenths of a trillion dollars per year. You're going to have a tough time convincing me to shed a tear over some oil infrastructure investor who lost money on an investment when I now pay $1.25 for milk that cost me over $4 just a few years ago. The total economic benefit of that expenditure is many times larger than the price tag.
THird - US oil production has essentially doubled during that period while peak oil true believers like the author here were insisting that it couldn't happen. That $280Billion facilitated about 6 million bpd of extra production (currently about $130 Billion per year) with every reason to believe that additional supply is still coming. Those who tout the rapid decline of production from fracked wells should also understand that many billions of dollars of that expended capital went to many thousands of wells that were drilled, but then caped without producing anything because current prices were too low. With higher prices, that's extra production that doesn't cost much of anything at all (because it was already paid for).
Lastly - There's nothing particularly new about this. The oil industry has gone through several boom/bust cycles. There's nothing there that higher oil prices doesn't fix quickly. Some firms go bankrupt and others buy up their assets for pennies. Then prices recover and the remaining companies make ridiculously high levels of profits (which are needed in order to cushion the next bust).