I think you answered your own question:
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...once in awhile you will hear him use the skill he has hiding and I know he could be close to age level if he just stopped acting "dumb".
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So I think you can go with what you obviously believe. Your subconscious is telling you he's faking it, even though you sometimes doubt that belief.
It also sounds like your choice of consequences is doing just fine, too His behavior gets worse when you let him get away with it, and his behavior gets better (quicker) when you stand your ground.
Another discipline idea might be to start getting him ready early for appointments (when possible). If he gets ready quickly, there's time for a special treat between getting ready and having to leave. So if he's fully dressed and has his stuff, you can stop for ice cream on the way. Or hold him in your lap and let him watch a few minutes of cartoons. Make the rewards totally worth it at the beginning, but totally random. Sometimes it's chocolate ice cream, sometimes it's a few minutes with bubbles. Then you can get him saving up - like three times of getting ready early in a row gets him a trip to Chuck-e-Cheese (depending on his age and motivation). Etc.
If he's older (school-aged and up) you could use cumulative consequences too. Like extra vegetables with dinner, because his brain must need more of them since it's not remembering things very quickly. Or going to bed early so he can get more sleep and move quicker the next day. Or you are "too tired" to take him somewhere fun he was hoping for, because you had to supervise him in time-out so often that day, and he has to stay at home with you and be quiet so you can recharge.
Hang in there!