The money involved with bitcoin is serious money and life changing money. But lets take a look at the only services that are managing our money:
1) MTGOX -- an absolute joke, incompetent, nonchalant about everything, " OH, you have 500,000usd stuck on our site, oh well".
2) Coinbase -- not as incompetent as MTGOX, but even more dishonest and fraudulent and gets away with it for now, because they are the only service of its kind. See this thread:
https://bitcointalksearch.org/topic/psa-coinbasecom-is-a-fraud-3410823) Bitcoin.org -- spelling errors, unsecure website, bitcoin qt problems, etc. Why is the main bitcoin client so hard to use? I have the best computer out there today and it is still unable to download the block chain without crashing something. I mean all the founders have made millions from newbies and they can't hire someone to fix up the original website/software?
4) alternate clients-- multibit works sometimes, and other times there are bugs. electrum relies on a server, and i've yet to use it.
5) All the other exchanges: bitstamp, bitfinex, etc.... they are offering good services, haven't screwed up royally like MTGOX or Coinbase yet, but they are still treading on thin ice.
For bitcoin to "make it", it has to go mainstream and be regulated. But for it to go mainstream, that goes against its original intended purposes.