"And I'm one of the more positive people when it comes to an aviation career. "
I really wish more people approached their job with a positive attitude. I flew with a captain the other day who was quite possibly the most depressing, negative human I have ever met. As soon as the door was closed it was non-stop complaining about unions, management, overnights, company policies, blah blah blah. If I never fly with him again it will be the best thing going. I am a firm believer that life is what you make it. If you don't make an effort to improve your attitude you will automatically gravitate towards the negatives. So the original question was could you be happy as a career regional pilot? I think you could be happy as a career cfi if that is what you wanted. Its just as easy to decide to focus on positives as it is to be a disgruntled, bitter person. As for the money, yeah its not the best but no matter how much you make you will always have money issues. And the last time I checked we don't go to our grave with our savings account so why worry. Just my 2 cents.