That's really an impossible question to answer. Way too many variables in an industry where 5 years is a lifetime. Here is what we know for sure.
Right now, the upgrade time is lengthy. There are almost 9000 pilots and it is a relatively young pilot group. The big retirement curve that is hitting the other legacies won't reach WN for another decade or so.
They are reaching the limits of what can be accomplished with the 737. There may be additional growth in the Caribbean, Latin America, Canada, Alaska, and Hawaii but it will be a tiny percentage of the network.
Today, the company does not do any redeye flying - no traditional transcon redeyes, and no JetBlue style island turn redeyes. The new reservation system will supposedly allow for that, so we can expect that over the next year or two the company will take advantage of it.
The new reservation system also allows for service only on certain days, or a few days each week. That might open the possibility to serve certain markets that can't support daily service.
The simulator building currently under construction in Dallas almost doubles the existing simulator capacity. Once it is open, the company will instantly go from 12 simulators to 18, and the building can supposedly accommodate up to 22. That doesn't seem like an investment that you would make unless you will have enough pilots to keep them busy.
New 'international' terminal is open in Houston and is under construction in Fort Lauderdale. Terminal renovations are almost complete in LAX and expansions in DEN and PHX are underway.
All that said...
The MAX will still not be delivered with a competitive cabin product - no power outlets or IFE, no meal options for purchase or otherwise, no premium cabin, boarding process that turns off families and business travelers.
The MAX will still not be delivered with printers or window shades
The scheduling system is antiquated and not compatible with the iPad without third party apps
Upgrades are driven by growth and retirements. We are forecasting that lengthy upgrade time based on retirements only. If you are new to this business than a good rule of thumb is 'don't believe it until you see it on the ramp'
WN has a history of eliminating competition through acquisition. Spirit, B6, Frontier, Alaska, Hawaiian? All good rumors and fun cockpit speculation. Any one of those would increase the upgrade time even more.
Age 67/70 would be catastrophic to WN first officers, many of whom would end up retiring from the right seat.
Another 9/11 would mean all bets are off. I would expect massive furloughs industry wide. Force majeur contract abrogation. The pilot shortage would instantly become a surplus.
So there you go. That is all that is in my crystal ball. If you think it's hazy now, I'd love to tell you a story about what the industry looked like in the mid 1990s. By the time you're ready to move to the majors, things may very well look very different than they do today.
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