Personally, my favorite portrait focal length on the 5D2 is 135mm, and the 135mm f/2 is a particularly beautiful lens; one of Canon's best ever. The bokeh is just gorgeous and it's quite sharp. That said, with my budget the lens I ended up with is the 70-200 f/4 L IS. It can't really hit a thin DOF, but at 200mm the background blur can be quite nice. I like the bokeh too, but not nearly as much as the 135.


Another lens you might consider for environmental portraits is the 50mm f/1.2. The bokeh is buttery smooth, and it turns out shots that just make you go "wow". If you're looking to stand out, the 50mm f/1.2 will definitely do it -- very few people can (or would) shoot portraits that way, so it's very unique. I do three quarter shots with that, but I wouldn't get any closer than that. Definitely wouldn't help you with your long lens problem. []