Let's look at the reality of the duration each phase of this 'pathway' would realistically take.
• Upgrade to Captain once reached ATP mins and 500 in type, assuming systems/managerial knowledge sufficient and one winter season completed
You're almost at ATP mins, so let's just start the imaginary clock when you hit 1,500. Let's also assume that you start Contour training the month after you get your 1,500 hours.
ATP/CTP + Indoc / ground/ sims will be 2.5 months (assuming no delays). Now you have to build 500 hours. I haven't a clue how much Contour newhires are flying each month, nor do I have a clue how their reserve system works and how long it take to hold a line, but let's use an optimistic assumption of 70 block hrs/month. Say 8 months. So now we're at 10.5 months. Add a couple weeks for cushion = 11 months.
• 1000 hours PIC at Contour=flow to SKYwest
Don't forget upgrade training, which will be a month (ground/ sims) plus a few weeks of Capt IOE (during which time you cannot log TPIC.) Let's say 2 months for Capt training. Now you get to start logging TPIC time. Let's call that 15 months. Add that to your already-accumulated time and now we're at 28 months.
• 400 hours in at SKW: guaranteed interview with United (or Delta or Alaska).
After 1600 PIC at SKW: Can flow to United/etc.
Skywest training will be 2 months (assuming no delays and that they hire you the same month you flow, which is a huge assumption.) You'll then be on reserve at OO, and depending on where you are, you might fly 10 hours a month or you might fly 90. FOs are sitting right now, and will sit as long as Skywest continues to shrink and CAs continue to leave. Let's assume you get 50 hrs/month so that's 10 minths at Skywest (38 months from when you started.)
Now here's the kicker: *if* you actually get that interview and pass it, then you've gone from CFI to mainline FO in just over 3 years. That would actually be pretty darn decent, and about on par with what young motivated regional guys have been doing recently.
BUT THE BIG CAVEAT is...there is zero guarantee whatsoever that you will pass that interview, not because of your own abilities, but because none of those carriers has any incentive to hire you, and every incentive to keep you at Skywest until you upgrade and grind out 1,600 PIC.
Let's look at how long that would take. We said it would take 38 months to get you from Day 1 at Contour to a mainline interview, right? Now add:
• 10 months to log another 600 hours SIC at Skywest (you need 1,000 hours Pt 121 time to upgrade. Contour is Pt 135 so none of that time will count, as far as I'm aware.)
• 2 months to go to Skywest upgrade training and complete Capt IOE
• Realistically 2 more years (if you work your tail off) to get 1,600 TPIC at Skywest
So now you are looking at six years from Day 1 at Contour to a mainline flow.
And that is IF Skywest and its partners abide by this agreement for the next 6 years. That is an utter eternity in the airline industry.
In the meantime, if you're fortunate enough to get a call elsewhere and you leave the program, you're on the hook for $$$$$$$.
Run. Don't walk.