For all the discussion of single-pilot or remotely-piloted aircraft, the simple truth is that even if those planes come to fruition in 25 years (very doubtful in my view, but that's for a different thread), that's about the average career length at the majors, which means that even pilots starting out today will probably not see those planes in their careers. This argument is moot, because even the most optimistic arrival of these planes will do nothing for today's problem.
What we have to deal with is today, because the pilot shortage is here today! You just have to ask at your local flight school, or at several of the regionals like American Eagle, or (as in the article) the Chairman of the Aviation program at UND. The students are not in training today. The airlines need to hire today. As the article pointed out, there will be a shortage in the short term, especially once the new minimum flight time requirements become active. Because the age-65 rule is now 5 years old, pilots will be retiring much faster than in the past five years too.
So for the OP back in part 1, yes, the pilot market will boom. There is no question about it. I've seen it first hand, and know what the airlines are up against. If you want to make a career of it, and have the resources to get through training, it's a good time to be a pilot.
One smooth landing is skill. Two in a row is luck. Three in a row and someone is lying.