Compared to some veterans, I haven't been in the publishing industry all that long. Three years and change is nothing compared to those with battle scars from editors that have long since healed. But compared to the vast majority of those testing the self-publishing waters, I've been around forever. I've seen at least different generations of would-be writers come and go on the various writing forums I frequent.
Self-publishing is no walk in the park. It's more than just the satisfaction of seeing your brain child for sale. It takes determination and infinite amounts of patience. It also takes a degree of humility to realize that maybe yours isn't the only story for sale nor the only story worth reading.
One really interesting aspect of self-publishing that I've watched change is readers. E-books are literally changing the way readers read and by this I do not just mean the physical entity in their hands. Digitalization has allowed the shopping experience to become far more efficient and it has also changed perceived market value.
I'm not going to go so far as to say that it's easier selling short stories. But it is easier than it was. Apps and subscription-based services are now a standard. With simple iPad games costing $4.99 and hit songs $2.99, it is no longer in the realm of "ridiculous" to be paying for a 50 page short story. In fact, I feel more and more people are starting to prefer this novelette length, especially if the story feels serialized like a TV show.
Who knows? Maybe short stories really will make a full comeback.