1. Automation....possibly may affect cargo operations but you should be able to get in a career before it gets good enough to replace pilots. Remember, right now they can't even do self driving cars because they haven't been able to program for human stupidity.
2. Yes I would do this again. I went thru bankruptcies, furloughs, etc. but would still do it. I really like having a seniority number and not having to play office politics. We have an old joke among pilots that goes like this: "You know you've had a successful career when you walk into the Chief Pilot's office to submit retirement paperwork and no one knows who you are"
3. I'm retired now in my 60's. Flew for a hobby starting in 1975, and for a living starting in 1981. For the 15 years prior to retirement I usually made in the low 6 figures.
4. I would have NOT cancelled my 1989 interviews with Delta and Northwest in order to take a job at USAir (aka the incredible shrinking airline).