Great idea. My desk job is a boring engineering job I really have enough of.
Afterburn81, would be happy to trade :)

My logic in using vacation days before resigning from my current job:

New hires are now required to attain a type rating in the aircraft that they are hired into. Back in the day, we could literally throw the gear for the guy in the left seat in the sim, fly a few single engine approaches and get tossed out to the line for IOE. This is no longer the case...newbies are now expected to be captains before they leave Flightsafety. This new rule is great for the pilot profession and for the flying public, but places a heavy burden on new hires.

Having a back up plan is a great idea. I would keep it to yourself though. No need to put any doubt into someone hiring you as to how serious you are about this. -- some might think it shows a lack of confidence, or that you'll just quit after the first bad day or two.

The first 2-3 months though at an airline can hardly be enough to judge what the next 5-10 years will be like. Training status is a world of it's own, as is being on reserve, and then finally a line holder. FO versus CA makes it a different job as well.

Thanks all for the feedback!
Here's another question. I may have the option to keep my medical insurance with my present employer for the duration of the leave. After that I would need to switch to the airline's plan. Is that possible?

Your plan is a very good plan, hopefully you can get all of the 4 months of leave because you are going to need every bit of it to make an informed decision.

I know you said that you "highly doubt" you will feel this isn't for you, but I guarantee you as time passes you will second guess yourself and your decision. You are going to be treated worse than you have been treated by an employer before. You are going to be around people who are constantly angry and if you hang around them long enough in the crew room I can virtually guarantee you will join in their misery. Your wife/family will tolerate this for a short time but will grow to hate your new life because you are never there. Your wife will now wear the pants in the family, she's the top earner now. All your money will go towards hotels, crashpads, and airport cars if you don't live in base. Don't get me wrong, you will be in the honeymoon phase for a few months or a year with the jet flying, the new uniform, etc..

With any kind of luck timing wise, you will make it out of training in 8 weeks without any delays between segments. Then you have your IOE. You are going to be in month 2-3 before being released to the line, and even then you'll be on reserve and who knows if you will even be flying.

This business is filled disillusioned pilots. Disillusioned “A feeling that arises from the discovery that something is not what it was anticipated to be, commonly held to be stronger than disappointment especially when a belief central to one’s identity is shown to be false.”

Like any job, there will be an open enrollment period. The exception to the open enrollment period is major life events like starting the new job, getting married, having a kid, etc.. Open enrollment is usually in the beginning of the year but I suppose its up to every company to decide on this period.

So no, you will need to make a decision on health care right away.

Based on my understanding of Obamacare health insurance portability *should* allow you to enroll outside of open enrollment in the case of certain life events...one of which is loss of an existing insurance plan. But obviously that would raise the question of why did you still have insurance with your old employer anyway?

AFAIK, healthcare benefits do not begin for 90 days at many regionals. So he proly will not have to make a decision right away...

Leave of Absence to go to a Regional
 

You have to disclose it, here's why. When listing you're previous employment they're going to ask for a start and end date, when your new airline verifies employment chances are they'll discover the discrepancy. This type of thing has ended badly for a lot of people.

Just be up front with them and they'll let you know if it matters. Most are so desperate in sure they'll work with you as long as you're not deceitful.

I know pilots hired in December just now getting IOE, how do you assure you can get hired and through training in 4 months?