I think this is the first time I've ever looked at your digital work, it's very photographic, from a distance especially it's quite indistinguishable. This kind of reminds me of those old text adventure games, the kind with the realistic painting-like backgrounds, not the cartoony ones.
Hey Joel, depends on what you are trying to do. Both at good, but I've never done much Painting using photoshop. The thing about Painter is that it was built from the ground up to emulate natural media --- various brushes, papers, etc. and is designed to have interaction between the two as well as a bazillion controls over how that happens. Much more so than in Photoshop as far as I can tell. The problem with that is that there is so much customizability that it can be overwhelming. For the moment I've decided and determined to become intimately familiar with the Pastel brushes. The latest release - Painter 11 -- has a new category of brushes called "Real" for the 'dry' media and they are even more like the real natural media -- not that the others weren't -- but it seem they act even more like pastels, chalks, pencils than ever before. The other thing I hope to learn is working with the knives. There is a guy David Dillon here on AP that does amazing things with them. [link] he too is here in the Denver area.
I'd encourage you to download the trial and see what you think.
I'll do my best. I'm really into this color/pastel/painting thing at the moment. I do hope to get some graphite going soon too though or get back to the one I'm partially done with - Wall Street Portrait...