Hes a gorgeous little pony! Connies are the best hey?
To me all these things that you say are scary to your horse, sounds like you may be anticipating that he is going to spook at everything maybe? When my horses spook at (for example, a wheelie bin) And you can feel them tense up as they near it, I would ignore the bin and just walk on past it. If the horse spooks at it, just turn it around an keep walking past it to get it used to it. I aslo agree with what Foxhunter said. Whatever method you prefer. :)
Good luck and lovely pony!
Cross Country- The act of hurling yourself and your equine partner at a stationary object with poise and grace while attempting to survive...