Voice of (My) experience...
From my point of view, I much prefer the stick over auto when haveing to use a vehicle in a heavy duty manner. However, it's a matter of experience (practice) more than anything else. In my job, I drive a Cement Mixer Truck, with what may be called an 18 speed manual trans. With all of the various gearing options, it's really a six speed unloaded and when loaded, I'll utilize all of the gears depending upon load needs. Back to the question. The only real problem I see with the stick is the innitial take off up the ramp. It's handy to use the emergency (hand) brake as you let off the clutch and release the brake at the same time. If the truck had a foot operated Ebrake it's more difficult. With the hand model it takes a bit of co-ordination but smooth is very doable after a bit of practice. (Large trucks have a lever mounted at the right side just under the steering wheel which is effectively a hand operated air brake which does the same job. Professional drivers use this feature every day). General driving with Up shifting, stopping on hills, downshifting will all require practice, practice and more practice. The benefits of a stick? It used to be a stick would get lots better fuel mileage. However, with the invent of variable stall / locking torque converters, that isn't so much of an issue any longer. Durability can be an issue depending upon the model of the automatic considered. Some automatics aren't very strong. However, some sticks aren't all that strong either. Then there's the clutch. Fairly easy to replace on rear wheel drive vehicles and may last a long time if you make it through the practice sessions. The other side of the story... I drive a stick at work. The last thing I need is a personal vehicle with one. But it's not because they don't act good in a tow vehicle. So maybe preference plays a substantial role.
Bill