This is actually a very interesting thread as I'm in exactly that position. 48 currently and after having spent 30 years behind a desk building a very successful business I'm feeling its now time to go fly for a living before its too late.
Not exactly starting from scratch though, gained my PPL at 20, CPL at 30 and fortunate to now have about 1100hrs, with150hrs multi / IFR time gained flying my light twin for business trips and pleasure so plenty of real world experience flying up and down the country single pilot IFR in a 6 lever twin (think one armed paper hangar!). By the time I negotiate my company exit, redo my ATPLS (long expired) plus all the other bits MCC / UPRT etc I'm likely to be very close to 50. I've made my money now thought so would be more than happy seeing out my days flying a Turboprop around north of the border with a bit of instructing on the side.
Yes I'm old and crusty but wondering if my real world IFR twin flying and a bunch of hours might make my CV stand out a bit Vs a freshly minted CPL holder with 300hrs or whether, as has been mentioned previously, most airlines would much prefer someone they can mould from scratch and my experience is actually more of a hindrance?
Regards
UA