Hope this thread is still relevant... I've been fascinated with Bridgestone - now Rivendell - bikes for 20 years, and recently, finally had the opportunity to test ride several Sam Hillbornes. A very nice bike to ride. I like to ride fast, and over as much varied terrain as possible short of mountain trails, but I don't care to look like I race. I have an older GT hybrid, and I've determined that I prefer more a road geometry bike that has some trail capability, as opposed to the MB style frame.
But like some of the other members, the final build price for a Sam Hillborne as I like is about $500 US more than I originally thought. Like the OP, the only other bike that seems to come close is the Surly Cross Check. I've tried a Norco and Kona Cycle Cross - nice, but the low handle position is lower than I prefer. Whether it's entirely true or not, I've bought into Grant Peterson's "country bike" approach with the handle at or even slightly higher than the saddle or the "expanded geometry" setup.
I haven't had a chance to test ride a Surly Cross Check nor am I likely to anytime soon. Can anybody comment on how it compares to the Sam Hillborne in terms of ride feel? I noticed that one member said the headtube on the Surly is fairly short.
I am aware that if I spend the money and time into customizing the Cross Check (moustache handle, bar end shifters, fenders, Brooks saddle, better rims, etc.) I might not be too far from the cost of a Sam Hillborne when all is said and done.