Hey,
The pathway to a flight career can be varied. I had a few previous careers prior to getting into aviation. I am currently a Captain at Skywest Airlines, based in SFO, 13 years in, about 12k hours.
I have been lucky/unlucky depending on how you look at it. As a multi career changer I started flying commercially later in life, I was hired at TransStatesAirlines in 99 and was based in STL then after getting transferred to FAT learned that the West Coast operation was closing and everybody was being recalled to STL. To be honest it only took a year of flying the J32 for TSA to convince that it wasn't worth commuting from SJC to STL to sit reserve. I colored in a Skywest application and was hired in spite of not being a CFI. I was initially trained in the EMB120 and when the CRJ was brought to the West Coast I transitioned as fast as I could.
I have sat reserve, been a line holder, based in MRY, DEN, and SFO. Currently am based in SFO and primarily fly the CRJ-700 as a line holder.
Lets be honest, as a pilot you are an expensive, blue collar(in drag) worker, operating heavy equipment. Management hates us, we are a necessary evil, but they tolerate us because we allow them to continue to operate insanely expensive equipment and make money with it, barely. If you want a graduate level education, go to Vimeo video hosting, and watch the Robert Crandall videos:
A Conversation With Robert L. Crandall (1 of 3) on Vimeo
A Conversation With Robert L. Crandall (2 of 3) on Vimeo
A Conversation With Robert L. Crandall (3 of 3) on Vimeo
These videos are about 55 minutes each, easily the most informative I have ever seen. My wife was even interested enough to watch them. Many do not like Crandall, but you gotta admit, he is good at what he did.
The industry is in for changes, the pilot shortage is finally here, age 65 extension was proof and now that it has run its course, all the hurdles you have listed will keep many from a job. Kit Darby was a snake oil salesman, and a broken clock is right twice a day, well one of those 2 times are on the horizon.
Do your own research, go to the FAA database, and compile a report showing how many mandatory ATP retirements are coming each year for the next 10 years, then go back and compile a yearly total of commercial certificates issued for the last 10 years. The numbers have been stagnant for the last 5 years and now the numbers are diverging.
Do the math, who will spend 65K for a job that pays $23.00 x 75 hour guarantee and sitting reserve in either FAT or IAD, and before you say I will, remember reserve means you are meat on a hook, that might not even touch an airplane, except to deadhead to a crappy hotel to sit TDY reserve 1000 miles from home.
Bleak enough? This job is not for everyone, it is a 24/7/365 operation, and as such having a life outside is difficult at best. I flew with a 25 year old F/O who was on his first divorce last week, but at least he gets to live 1000 miles from his 2 year old son. If you have a girlfriend/wife are you prepared to find another? This job cost me a 10 year relationship, because she didn't understand the job, my 12 year wife does.
If you are doing this for the money, you will be sorely disappointed, it's not worth it. If you think sitting in a cubical is a slow miserable death, it might work for you as long as you remain pragmatic. I continue because it works for me, I would not recommend it for anyone, you have to decide for yourself if its worth it, it's a crap shoot on the best of days.
Society is littered with the victims of the airline industry, it's a mean, vicious, human grist mill that grinds people up into little bits and chunks. Survival of the strongest rules, with a healthy dose of luck(timing) it might work for you. If you think anybody or anything owes you anything, you might be disappointed. If you believe that you only get what you can negotiate, you might make it.
Good luck
eric
P.S. I fly a CRJ for money, and a Kitfox IV w/Rotax 912 for fun.