After working a bit this morning, things are starting to look more resolved. In fact, at this small resolution, it look almost finished. Well let me jot down my self-critique notes, and we'll see how it shapes up.
1.) I'm using a brush that's too small, it's getting "fussy" in areas.
2.) Jack (the dog) is a bit too pudgy.
3.) Shadows on grass need to be resolved into landscape. Right now they are too much of an element.
4.) Detail in woods (hints of light areas behind trees, etc.)
5.) Tighten up "portraiture"