After I obtain my private pilot certificate, the first thing I'll probably do is upgrade to a more powerful plane. Let's face it, I'm not exactly a light person. More power means I can take up other people. I want to share my experience with others and introduce them to flight. I think I will be happy for a while like this. I might try other planes, but really I think I'll just enjoy flying in good weather and cheaper planes for a while. I would like to go places I haven't gone and see things from a perspective I've never seen.
Eventually I envision that I will get my commercial and instrument certificates, but in what order I'm not yet sure. And when I do this is also up in the air (oh that's so bad...seriously, no pun intended). Once I start to feel a need to fly in the clouds, then I'll consider the intrument ratings. And once I'm ready to make money flying, that is when I get the commercial rating.
Looking forward twenty years around retirement, I envision that I will make flying my retirement job. I think I would be happy toting cargo, giving aerial tours, or island-hopping in Hawaii. I'm sure the pay isn't great, but I that's not really the point.
I've gone back and forth on owning my own plane, or maybe even my own fleet. The way I understand it the cost is quite high so partial ownership or a leasing plan might be the better way to go. I have realized, though, that I would probably leave the bigger more expensive planes alone. I don't think I'll have need to own my own four-seater, when I'm just flying for fun. I would rather save the money and rent larger aircraft when I need to.