Great question Alex,
The answer is yes, there are pilots who stay at their Regionals for life. The 2 main reasons people move on to the Majors is a) Pay (as you mentioned) and b) the desire to fly a BIG plane around the world. For me it was the latter. To be honest I was very happy at my Regional. I was senior, had a great schedule and made pretty good money (over $100k). If they could’ve given me a guarantee that I’d keep my Capt seat, at my same base for the rest of my career I would’ve strongly considered staying.
As I said I did have the desire to fly a big plane to some exotic locales but more important it was the volatility that pushed me out. You see Regionals don’t sell their own tickets, they have contracts (CPAs) with the Majors they support and those CPAs expire and change. Sometimes they get better deals and there’s expansion but sometimes it goes the other way. As I said I was very happy at my Regional for a while but one day we lost a bunch of flying to another Regional who underbid us and the next day there were furloughs, downgrades and base closures. The thing that really freaked me out was I was on a crew shuttle with an older (60) Comair pilot (previously Comair had been a TOP Regional). Comair was in negotiations with Delta and Delta wanted MAJOR concessions. All he kept saying was he wanted the airline to continue for another 5yrs so he could retire. 2 weeks later Comair shut down and this guy was on the street at 60. Not cool.
The reality is the airline industry is far from stable whether you fly for a Major or a Regional but at a Major the airline is more in control of it’s own fate rather than being dependent on the fate of another entity. That does seem to add some stability. Bottomline I have a few friends who are still at the Regionals and plane to retire with them. They’re happy and have great lives for the most part. That said my friend Paul who’s been at his for 20+ years finds himself having to move after 20+ years because they’re closing his base. But Paul is still happy, pretty much.