Farmer's markets. The people that go there are idealistic about independence from big government/big corporations but are usually grounded enough to understand a bit about economics since they have successful businesses.
Yep, though bitcoin has to come a long way till over-the-counter purchases are convenient enough.
Not that long on the consumer side: BitcoinSpinner is pretty much the perfect solution (a little rough around the edges, but should be amazing within a few weeks) for Android users looking to carry around BTC for everyday spending. On the POS side, we definitely need better solutions. Maybe another Android app, very much like BitcoinSpinner, but one that takes into account inventory and prices and exchange rates and merchant fees and... well, lots of stuff. The concepts are there; the implementation is not.
I just thought of this (possibly not quite legal) idea. The person operating the stand would generally sell things for less in BTC than in fiat (assuming they take credit cards or have a way to evade sales/income taxes on BTC income). Then s/he could also exchange BTC for fiat for customers that have fiat but want BTC; like currency exchange or just giving change. Or better yet, prices could be lower on BTC transactions but for fiat transactions (especially ones paid in cash where there are no credit card fees), the person could give a "free gift" of the BTC price difference to the buyer to encourage the BTC to be spent either at the stand or at other BTC-accepting vendors.
