Humble

That's a question best left for the chief pilot. Candidates are evaluated on a case-by-case basis. I'd recommend opening a line of communication to introduce yourself and see if you and the company would be a good fit.

It depends on a number of factors. The CRJ currently operates on "scheduled" runs from TVF to MEM. I'd assume those guys fly around 20 hours every week so about 80-90 hrs/mo. I'm not sure how many crews they are currently operating or how the crews are handled over weekends.

The 727 is purely on-demand. If it's a busy month you'll likely riding the maximum you can fly ~120 hrs/mo. If its a slow month you might see as little as 40 hours. On top of all that your schedule will affect how much you fly. All of the numbers I've discussed are for a guy who is always on call (they do try to release on-demand guys over weekends if a crew who is on the schedule is available). If you are 2 on 2 off then obviously you wont be flying nearly as much. Keep in mind if you want the 727 you will be based in PTK and will need to live within 20 minutes of the airport.

There was when I started. You sign a 12 month promissory note that is proportionally forgiven over the 12 months after you complete OE. It might be different now - worth asking the chief pilot.

IFL is changing, trying to react to the high demand for pilots. As it stands you have 3 schedules available to you - always on call (again, they try to release you over weekends if other guys are available), 2 weeks on 1 week off, 2 weeks on 2 weeks off. Hours flown, pay, QoL varies with each schedule. Take all that with a grain of salt though as things are just as likely to change. If everyone went 2/2 they would have to hire a ton of crews.

Best advice I can give is to introduce yourself to the company and get answers straight from the chief pilot's mouth. Good luck.