Earlier quoted context omitted.
Also, hopefully, more money/financial security with a bit of age. I am nearly 34, own own house, car, etc etc... nice to have that bit of security. But I guess in big cities you are a wage slave for a long long time, so its a harder jump to make.
If you don't own them outright then your financial obligations actually give you less freedom. When you have nothing to lose, that's when you swing for the fences.
Swing for fences means "take a chance" I assume ?