Jbarcs, I'd be inclined to see if there's a double crankset that can give you a 28-30 tooth small ring and 40-44 big ring. 11 tooth small cogs give you a huge high gear with any chainring above 44t and a small front chainring is the easiest way to get low gears.
It seems the Sugino, though spendy, is one of the few cranks that fit the bill. I use an OX601D that I got from Hubjub, Sugino OX601D crankset, and have a few different ring set ups for it but have settled on the 48/32 for commuting and around town and will drop to a 46/30 or 44/26, if I decide to load'er up. I currently run a 11-36 cassette but the 11-40 sounds appealing to have a bailout for steeper ascents, common in my part of the world. My ideal would be a 12t high with a tigher spread across the middle range and have the 36 and 40 be bigger jumps but I'm sure there's a reason gearing like that doesn't exist. As was pointed out by someone else I too find that my natural cadence falls slightly between my current gearing on my bike and I find myself shifting back and forth between two cogs on longer rides.
