Nice idea. It can work. From the story point of view I would bring the conflict earlier. As Zensteve says, it gets a bit repetitive, and I think that there is more potential on the conflict of the painting cheating with Lilcoln(?) - that was pretty funny -
Also you can use more theater like talking, so it's clear that you are talking and not the painting. Chaplin's movies are great examples (lately I have been revisiting them all).
Also make sure you are in frame, you get out at times and it was pretty blury.
Still filmed by yourself it's pretty cool an imaginative! Sure you can make a pretty cool short there. I liked the idea that you went for a silent movie (thinking about it on my next project).