I have seen the farms of Salinas. I have been to the coast of Monterey. To me, Steinbeck is the American novelist, and to have a greater context of his upbringing and his work is a powerful experience. This is an incredibly privileged job, I am slowly seeing the country without spending my own money...that part changes later this summer. And yet, it is a feeling of place that I am unable to attain.
In 2013 I found myself simultaneously single and on the academic job market for the first time. I was thirty, several years into graduate school and at work on a dissertation about nineteenth-century poetry and pleasure. Literary studies, my dissertation argued, was blighted at its core. It had forsaken pleasure, the very reason most people devote their lives to literature in the first place—and the likes of Shelley and Hopkins were apostles of an enlightened hedonism that promised a way out.
Who would you rather date? Who would you rather hire? Who would you rather have a beer with? In the examples you list, the problem is not superabundance - the problem is that no amount of technology will ameliorate schlubbery.
Eating dinner alone is a privilege, not a burden. You become vastly more interesting to the staff and you have an experience that's all about you. When I was down in LA the first time I was a regular at five or six different restaurants. They knew my table they knew my order and when I was there with a friend or a colleague or my wife or whatever I got treated well.
One does not find a strong community. One creates it. This starts with the confidence to dine, to vacation, to dream alone.