My take on the man's story is he needs to relax and enjoy (which he is) to see where it leads to, no point in looking down the road or thinking what might have being, and even if you don't make it soo what atleast you can boast that you hold a PPL/ATPL (whatever the case may be) license surely many a people whom you probably know would never dream of YET still achievable. I find myself in a similiar sort of position (27) and also set to take the plunge into flying and I am already in a good financial position, single, living at home, little or no bills, don't smoke or barely drink and can save guts of atleast 5K a year on my wage yet I still get negative thoughts because of the the way the industry is going and the fact I work in a factory which is never a lifetime job in most cases, I plan in taking a trial flight at the start of summer and I will know if its something I really want to do. But if you ask me you sound like your very enthusiastic about your flying at running a business and being a family man at the same time says alot for ambition. Best of luck