"Easy" if you have an unlimited supply of replacement shocks and rims, and your uncle who owes you money runs a repair shop :p
I've only drove SB to the Loaf once and it was an easy and gentle drive. The roads leading to Rangely from the south and west of the mountain are absolutely nasty in the winter.
I haven't been to the Rangely area since May if 2016 with Saddleback being out of business. But the Route 17 region around Height Of Land was always really awful, with lots of broken pavement and potholes. It's only 75 miles to Sunday River from Saddleback, but it takes almost two hours.