Here is a paper that shows the kind of work being done on the "reverse engineering" of brushstrokes (the field is a bit esoteric):
http://jivp.eurasipjournals.springeropen.com/articles/10.118...
And there is a lot of work available on brushstroke analysis for authentication purposes. Here is a pop-sci example from about 8 years ago:
http://www.pbs.org/wgbh/nova/tech/art-authentication.html
Additionally, in terms of desktop graphics editors such as Photoshop and Illustrator, rest assured that Fractal Design Painter definitely had a model that incorporated (well, approximated anyway) medium, angle, brush size, pressure, direction changes, the color you were painting over, etc. 20 years ago, and the latest version of Corel Painter has added features such as particle systems and modeling individual bristles (and other features have been added in the interim).
The intent in Painter is to enable the creation of new works in a way that feels natural to artists used to traditional media (not to mention reproducing the appearance of those media), which isn't quite what we're talking about here, but hopefully this demonstrates that such models do actually exist.