Have you considered doing a different hood (neither stainless nor matching the cabinets) to make it a focal point? In a small galley I'd go with the least obtrusive (match the cabinets, or stainless undercabinet). In a large open kitchen (i.e., in a great room or simliar) I'd go with the same thing. But in a large, squarer (vs. galley) kitchen, I'd use the hood to introduce a punch of color, even if it's a neutral like black (perhaps with stainless banding).

Re cleaning the wood, it depends on how good your insert is and how ornate the wood is. Lots of appliques with high relief grapes and vines, for instance, combined with a lot of billowy, greasy cooking (tossing wet food into hot oil for instance), so that the vapors escape the hood catchment, could be a real nightmare. A simple design, wtih less aggressive cooking, should be fine. As with all other cleaning, it helps if you attend to it early and often, rather than waiting until you can see the crud.

We faced this dilemma as well, albeit in a 1950's cape style home (white glazed cabs). We ultimately chose the custom wood hood and have been thrilled with the look. Ours was patterned off of charlie123's hood in the finished kitchen blog (there are two listings and it's the second one). It's really a personal choice, but we oversized the hood as recommended by many of the cooking buffs here to 42"W x 24"D for a 36" pro-style rangetop. In doing so, we thought the huge stainless hood would look out of place with our more traditional looking house.

In terms of cleaning, if you size up the hood it does seem to capture much more of the steam/smoke, thereby leaving less to collect on the outside of the hood.

Thanks so much for your input! We decided to go with the custom hood. I agree it will look better in an older home like ours. I also like the idea of making the hood a focal point. I have a nice collection of brown transferware that I want to display in the kitchen, so maybe I can incorporate a plate rack in the design of the hood. I really appreciate your thoughtful suggestions.