In my opinion, the best time to get into the business is when there is a lot of negativity in general before or at the beginning of a hiring growth period. If everyone wants to be a pilot and the majors (as a whole) are hiring thousands a year and you're just starting our. Your probably getting in on the end of a growth spurt and historically you're probably looking at a cyclical down turn and years of stagnation. The opposite is usually true during bad times.

Just my thoughts.