I threw caution to the wind only yesterday, when I sold off most of my fleet (with the exception of my Courier and Clipper - I don't have the naval rank to buy them back) just for fits and giggles. It took half the evening to fly about and get them all, but I was left with a tidy bank balance as a result.
Nothing like a billion credits or anything, but it was enough to buy a Conda.. I couldn't help myself.. I was at a system where they're cheap, and got 20mil for my Asp.. 100mil Conda? Yes please.
I managed to spec it for trading too, and almost lost it immediately when I got it wedged in the docking slot.. Words were said, deities where beseeched, and underpants were soiled for almost a minute, until I somehow managed - with brute force and ignorance - to power blast my way free, with literally seconds to spare before the mincemeat factory opened. Needless to say, I bought a docking computer and safely tucked the Conda in storage until my testicles grow back.
I also picked up, on my own father's recommendation, a FAS and A-specced it, to replace my Vulture. A fine combat ship it is too (over 1800 armour!!!).
I also bought another Asp and smuggle-specced it, because I have now fully embraced the life as a slave trader. I'm sorry, but if mining could pull in 50mil credits in under 3 hours, then mine I would.
25 ships down to 5. Not quite the "Sidewinder Start".. yet, but I have definitely enjoyed spending my dirty, ill-gotten money on expensive ships and outfitting.