Shon
Age must be another consideration. If you have a successful career I would be guessing that you are no spring chicken.......could be wrong and apologies if I am, but if doing it 'slow time' is going to take you another 5-10 years then that has to be a factor when contemplating your chances of gaining that first flying job. I'm not sure about things in the US but I thought it was much more structured as regards flying jobs; literally starting small and 'doing your time' on each size of aircraft before eventually getting onto something big. That of course brings another factor into the equation - what are your goals, where do you want to end up, what is a realistic timeframe to achieve that and will you be 'over the hill' in the eyes of the recruiters by the time you get to that level if you spend too long getting your licences issued?
So, as with all these things there is no 'right' answer, it's personal preferences and tough decisions, usually spattered with a reasonably large dollop of risk and hopefully the determination to succeed.
So try thinking out a plan to achieve your goal(s) and then put a timescale on it. It may become evident that unless you get your licence issued in the next couple of years that you may not be able to achieve these goals and even if you can the financial risk may be too great.
Regards
PP
Sitting on the fence and trying to see both sides as usual!