Sure, the art direction might work since paintings are often used as money laundering. It might be hard for them to get any information related to where the painting is going to be taken, and that would be very suspicious if they started asking really specific questions like which roads they were planning on taking the painting. Maybe they could inquire where the sellers usually keep their painting, or find out where they live so they could burgle the house or storage building later on, since she's great at lockpicking and Shay can do more physical tasks, like helping her hop fences, subdue guards, that kind of stuff.

I think easy's fine, they'd want to test the waters with Vera. It wouldn't make sense to throw someone untested against something above her skill and experience right away. Plus, narratively speaking, it's nice to build up to bigger things.