Both have its advantages.. remember, the second option is flying for *fun*... it's purely fun.. the other is work.. it's a pretty cool work.. still it's work..
I'm sticking with the fun part for now.. but am more than open for the other option
We'll see how it works out.. I'm not in the position to just drop my IT job quite yet...
Paying off mortgage (instead of buying the plane you mentioned).. and then living off of S.O's salary while you go through advanced training can be an option.
(btw.. whatever that "you're not capable of being in command" comment was all about..)