NEW 07 sTT, purchased oct 09 with 12 miles on ODO. now has 3500 miles. No problems with mine at all. kinda forgot about the first maintenance and had it performed at 2200 miles by HD/Buell dealer (they were VERY nice - but they are also a race shop with HD drag bikes and even a rare Buell "Cup" bike from the single make series back in the early '00's).
I have not ridden in rain, but did about 50 miles of dirt/gravel roads one day and then road another 200 home after that - bike performed flawlessly.
the only real issue I've had (and thus learned my lesson) is NOT to start the bike, blip the throttle and then shut it off and not run it again for a few days. It definitely will cause the plugs to foul on the restart. Best advice is to turn it on and immediately ride it. Even in cold weather.