How well does being a pilot pay, eg. entry level and at the 2, 5 and 10 year marks?
The number of years it takes to go from regional FO to major Captain is extremely dependent on the economy. Since everything is based on seniority, if there is a downturn, airlines fly less flights and need less pilots, so basically your career goes on hold because no one is getting promoted. When things are good, you move quickly up the ranks.
To your direct question, once you have all of your ratings and your 1500 hours, plus a 4 year college degree (required at major airlines) (figure 6 years and $200-250k in debt), at 2 years you are probably FO at a regional, $50k/yr. At 5 years, captain at a regional, 80k/yr, 10 years, FO at a major, $150k/yr.
If the economy tanks, you stall and might be laid off or furloughed. If your airline goes bankrupt, you scramble to find another job and start at the bottom of the FO totem pole again. If you have almost any health problem or require most any medication, you lose your medical and find another line of work. If further automation leads to a single pilot cockpit (fairly likely IMO in the next 20 years), you either lose your job or take a big pay cut.
First officer salaries at regional airlines have come up to start in the skilled trade range, $60k plus. Regional captains make $80k and up. (It used to be awful, $20-30k.) Getting to that point in the Part 121 world takes a lot of training and expense. Candidates for the Airline Transport Pilot (ATP) certificate must have a minimum of 1,500 flight hours.
Other commercial flying such as hauling cargo, air taxi, or private charter may require a commercial single or commercial multi certificate with instrument rating. These pay about like the skilled trades too.
Reaching ATP minimum required 1,500 flight hours has multiple routes to it. Unfortunately for people who work their way up through the ratings as civilians, they are competing against retired military pilots who did not go into debt for their training and who are receiving pension payments. (Military aviators certainly paid for their training in a different way, and I am making no comparison of their respective costs.) Retired military pilots are frequently hired directly to major airlines whereas Billy and Susie Civilian start off at regional airlines.
Even with ATP certificate in hand, it’s not yet fat city. Airline pilots have to work their way up through the seniority ranks, beginning with crummy ready reserve where they sit around hoping for a ride. Other flavors are short call and long call, the difference being how quickly the pilot must report for duty after receiving the call. Moving up to more desirable bases and aircraft goes through a complicated bid process[0].
[0]: https://www.reddit.com/r/flying/comments/8eaupt/moronic_mond...
Yes, compensation relative to the training expense used to be horrible for first officers and even captains at regional airlines, starting in the $20k range annual compensation. Again recall that military retirees have their mailbox money coming in. Because of the pilot shortage, first officers at regionals now start around $60k annually.
Two common civilian paths to ATP minimums are becoming a certificated flight instructor (CFI) or flying aerial survey, photography, air tours, private carriage, diver driver (i.e., flying skydivers) and so on. In reality, there may be some blend because all of the aforementioned tasks require a commercial pilot certificate. Because the airlines are a training environment, there is at least some degree of preference for CFIs rather than someone who schlepped around for a thousand hours towing a banner over the beach in a 152. These are not minimum-wage jobs. Someone with a wet commercial ticket might make twenty bucks an hour. Here again, the would-be ATP is competing against fellow time builders trying to get to 1,500 hours. More advanced instructors (e.g., CFI-Instrument, commercial instruction, or complex instruction) command a higher hourly rate, and instructors get paid for both flight time and for ground instruction. It’s not great money, but they aren’t starving either: starting in the $30k range up to the $50s — a lot like apprentices in the skilled trades.
Candidates for the commercial pilot checkride must have at least 250 flight hours. The commercial airplane ticket comes in four flavors along two axes: single- or multi-engine and land or sea. The least expensive is airplane single-engine land (ASEL). To reach that point, trainers in this class rent between $100 and $200 per flight hour “wet,” inclusive of fuel. Include instruction, test fees, gear, and the cost of an instrument rating (which I am glossing over) will total to around $30k. Some flight schools and operators of multi-engine aircraft will foot the bill for the multi rating and MEI in exchange for some number of flight hours on the back end with a clawback if the pilot leaves for another opportunity.
I would love if someone in the industry could shed some light here. I have two friends early in an ATC career and it sounded like getting to where they are now was hell (and they definitely aren't at the 6 figure mark yet). The most reductive way I've had it explained is it's years of training, with shit pay and relocation, and the possibility of washing out along the way being relatively high.
Assuming our hero passes the academy, she is then assigned to an Air Route Traffic Control Center (ARTCC or just Center), an air traffic control tower (ATCT), or an “up-down” facility with both a control tower and TRACON, terminal radar approach control. Certifying in just one sector may take a year or two. Trainees make upwards of $30k annually. Someone who washes out may look at transferring to a less demanding facility. People also request hardship transfers to be closer to family and so on, but ATC is chronically understaffed, and obtaining those transfers takes time.
As with pilots (see another reply in this thread[0]), military ATC experience is often a more expedient route. FAA controllers tend to discount the skill and decision making of former Army controllers who mostly deal with low-flying slow movers under VFR rather than jets under positive control.
[0]: https://news.ycombinator.com/item?id=16941169
Oh by the way, our hero must get in (I believe be admitted to the academy) before her 31st birthday. The clock is ticking.
Yes, there is survivorship bias in the success stories. People wash out of other careers too. Seeing actual data on rates would be fascinating. For balance, read the “Why do drug dealers still live with their moms?” chapter of Freakonomics.