Lol, i like this direction for the thread, but I'm probably going to be unseated as the biggest looser too... I've deposited approximately 1,200 US in the past year (but part of that gets skimmed off in the transaction so actual money that went into game is less) and now have just over 30k skills and only about 200 US or 2k ped worth of stuff. I took about 6 months off in that time though. I'm contemplating depositing my way onto the top 100 skills list over the next couple years lol.
for wasting money and loving it
not through actually working for those skills but just buying up chips on auction... well its better than giving all away to beer, hookers, and blow... at least I'll have a good pile of skills in the end, no nasty diseases, messed up sinuses, or a huge beer belly.