The way I see it, expertise has qualitative and quantitative aspects to it.

The qualitative aspect relates to the depth of knowledge of a person or a service and how well they know me as a subject. It has a lot to do with trust too. Why did the service offer me these snowshoes? How do I know it’s any good? How do I know the service is any good?

The quantitative aspect relates to anything countable that relates to trust (stars ranking, years of experience, awards etc.)

Considering these two aspects with the products you had mentioned, I believe you could get to a better decision faster, using other non-conversational UI services.

Mature AI — will be the game changer. When my body measurements will be scanned and uploaded to the cloud, along with my current wardrobe and analysis from my social media photos and last purchases, I will be sure that this product that the service offered me is the right one.

But until then, I think it’ll be hard to go around the quantitative knowledge base of Amazon and such. The trust we have in the masses is higher than our trust in complete strangers on the other side of the chat.