I'm Young (26), zero debt and no family.
At the urging of a good family friend (Fedex 777 CA) I have chased the quick upgrade by leaving one regional (S5) for another. (YV)
Would I recommend that to a guy with family and 100k in debt? Heck no!
I think everyone's situation is unique.
Either way I'll let you know how it worked out in the next 6-12 months.