Jeff, thanks for the advice! I've considered apprenticing myself, but my 9-5 (well, 7-3) gig interferes with being able to truly dedicate myself to another profession on top of schooling and being with the wife - but I'm focusing on schooling to try and get me that greater edge to nudge into the finance market.
Dyan, I'm focusing on CPA/CFP - I've done sales in the past, I'm wary of giving stock advice, invest only what I'm willing to lose (...mostly) and do some analysis on my own. I'm more interested in being able to help people but like the idea of being a Financial Planner a bit more than just being an accountant - but I have a feeling I will end up doing accounting work at some point as I transition.
Latro, thanks for the good advice. I think I'm stressing a little too much over my current job and need to focus more on the skill sets I can further develop and pair up with finance in future jobs.
Ultimately, being my own boss is my goal (isn't it everyone's?) - I'm slowly working my way towards it, but I've gotten some recent "doom and gloom" readings from certain people I'm affiliated with that make me cautious in staying in this area for longer then I need to (I'd rather take a life boat than be left with a jacket). I'm attempting to be prepared should the boat sink sooner rather than later (preparedness makes us powerful, butter merely makes us fat).
Of course, I could totally be wrong...