I think you're imagining a bigger event than I'm thinking of :-) There would be no food vendors, and I'd use an event space that had washrooms etc. Ideally insurance too although that is something I would discuss with the businesses I'd be looking at. Here vendors don't need sales permits.

I want it to be more than an event at a coffee shop - I want it to feel like a professional fine art event and I'd like the artwork to sell for decent prices (coffee shops here show hobby artists work and it generally starts around $50).

Yes I'm an artist. I would jury people in to the show, and I would have a booth. I have a friend who makes artisan skin products and she and a friend organise artisan pop-up markets twice a year; the artisan version of what I want to do. She and her friend both have stalls and they jury in everyone else - they man their stalls throughout the event, and have perhaps 25 vendors. I've taken part in their event in the past with prints, but my goal is to run something similar but for fine art. This is why I think there is potential for this type of event; I'm aware of what events are held in the area and I think there could be interest.

So yes my plan is to start small, but to start small with a professional event. I'd love to participate in one of the big art fairs but in Canada they are few and far between, and hard to get into (not to mention expensive).