I expect that at some time soon, our local wine retailer will (unsuccessfully) try to sell olive oils. Probably boutique imports with a local 'winemaker' variety thrown in.
The only way I could see it working out for them would be that they include an oil & bread alongside wines at their weekly tastings.
I still have my doubts but if the oils are clearly tastier than supermarket offerings, they will sell.
BTW the nation's largest (and dysfunctional) retailer is selling Spain's Carbonell brand EV 4L for $20 as a promotion instead of $40+; hard to beat!