When I started offering a subscription to artwork through Home Gallery Project I assumed people would be rational when considering the price. Big mistake.
First, price anchors are very real. Customer after customer anchored their purchase of artwork to other purchases in their home, like their couch, TV, and bed. However, when considering a monthly subscription to artwork the anchor was always Netflix. $7.99 per month is just too little to pay for shipping, let alone the artist.
This has an important implication: people with more expensive furnishings also buy more expensive art. If as an artist you want to price your painting at $5,000, sell it to someone who has bought a $5,000 couch.
Next, people in apartments guessed (often incorrectly) that they would only be in their apartment for at most another year. This means that when considering an annual plan, they compared it to purchasing artwork directly. And it turns out that owning the art is important, even if it will be thrown out after a year.
The elasticity of demand is also interesting. While a specific piece might be a must-have for someone, an unknown piece is at best a nice to have. This means that there is significantly more price leverage once someone has decided that they want a specific piece. With a subscription that isn't tied to any specific piece, the leverage simply isn't there.
The successful art sellers all seem to have the same playbook. Build up a list of people interested in art who are in the same socioeconomic bracket and similar tastes, then periodically invite them to events. At these events, have a great salesperson who can convince someone that they want one of the pieces.