Hi inkleberry,
Thoughts and ideas:
I think you have to try to pinpoint the source of the problem. Is it the motion of riding in the car or stroller, is it something about the enclosed feeling from a car or stroller, or is it the position of the car seat? These are the three options I can think of, but there could easily be something else.
Would he begin to fuss in the car seat no matter where it was? If you put him in the car seat in the crib for example, or someplace else where he is otherwise content, what would his reaction be?
If it’s the motion of the car, maybe being put into the car seat is all the notice he needs that the dreaded motion imminent.
What if he is looking at something which holds his interest (classy little fellah that he is, give him some Van Gogh again) and then snuck into the seat? If he cries immediately, it would seem to indicate that the seat itself is, in some way, bad for him. [I had a car a few years ago that I finally had to sell, simply because I could not get comfortable in the seat, in any position.]
If he tolerates the seat while it’s not in the car, then I guess you narrow the field. Does he cry when the seat is put in the car, before the motion begins, or after?
Is he afraid of the enclosed feeling he gets in a car or stroller?
And then there’s the direction you have him facing, which has been mentioned.
Our youngest daughter HATED travel which lasted longer than fifteen or twenty minutes. She made us dread driving the 45 minutes to and from her grandparent’s house. She made it sheer misery, and I might add, dangerous too; you just can not concentrate on your driving when the child you love is telling you that they are in mortal danger and need your help. I remember one trip all too well…but no need…
Anyway, look at all the variables and then start testing. Try to make sure you really know what it is that the little guy hates, and then see what you can do to alleviate his misery.
Our youngest still doesn’t like extended travel, but she has come a long way. We are no longer prisoners in our own home. I am sure you too will work this out, or, it will work itself out.
Hang in there.