I too am the 3rd generation and knew what I was getting in to. If you are set on it, you need to make it your 100% focus and give up on the young party crowd and social life. I took several chances in my career and so far they have paid off, but it was miserable for most of my time at the regionals. You will always be gone and commuting makes it worse. I was doing either a 3 leg commute, or a 1 leg with a hour and a half drive (outstation based) with 11-13 days off a month. Some stretches of being gone for 14-17 days at a time. You will lose touch with your friends, your significant other will get sick of you being gone unless she is extremely supportive ( I got really lucky there), and the pay is sh!t.

It is true when most people say this job sucks the fun out of flying. I was like you and could not wait to go fly next. Now, I can't wait till I am home and off next. Granted, I am based at home and on reserve, and not being used much, but I am not truly off. I can't stray too far from home, go grab a drink with friends, make solid commitments in case I do get called, or generally have a life. You will work the opposite schedule as your friends and family but on the plus side the m-f commute sucks.

Now with all that doom and gloom said, I still love this job. It may not seem like it, but I really do. I cannot see myself doing the m-f 8-5 office job. I got enough of that during training. Most people I fly with are great, the destinations are great, the eventual pay and time off will be great but there is great sacrifice on the front end of this career. If you work hard, keep your nose clean, build your network and connections, hopefully it will all work out. You will never know if the choices you made were the right ones until the day you retire and look back on it all.

In regards to your question, if you pick a place for a quick upgrade and things go south in the industry, is that a place you can see yourself staying for quite some time? The quick upgrade today, will not be tomorrow. I went for the quick upgrade after several years at a different regional and it worked for me. But shortly after I left they were downgrading and displacing. You just never know what will happen to the place you go.