I suppose the benefit (for some) of the San Jose is that it is Steel.

I am considering a Jamis, maybe the 4.0 for the Alfine and Disc Brakes. Or the same model you purchased. Despite the junky fenders, $560 sounds like a good deal for a Nexus 8. Make's me question if $200 more for the Alfine/Disc Brake model is really worth it?

My main reason for wanting one is that it is Upright and has an Internal hub.

How was it as a upright commuter? Comfy? Work well with the cushy saddle?

My Fiancee is considering a Amsterdam Royal 8, because she loves the style and felt very comfortable riding it. Not to mention... she could wear a skirt.

I thought the Jamis, with it's larger oversized saddle(I read this style saddle is better for women?), might be a worthy consideration as well.
The Redline R530 is on the short list of test rides for her to, the Birias with a step through frame ($750 with a totally step through frame, 8 spd Nexus, hub generator lights), and Electra Townie (although she MUCH prefers the look of the Amsterdam!).

How about using Rapid Fire shifters with a Nexus? I love Rapid Fire on my GT Hybrid.

Nice Ride!