Ho Matt
I also also used to become somewhat disoriented when scoping out a general area by eye while under the guidance of a star map. Translating positional data from the page and then looking up I had no trouble with. I could recognise markers, asterisms and general angles and lengths to find where I wanted to point the scope. Once I looked through a finder everything changed. The field of view was far smaller, so references that I stored in my head dissappeared out of view and i became lost.
I fixed this disorientation in two ways.
1) A red-dot finder is 1:1. No magnification to throw you off, and you can just peer through it from behind to position the infinitely-focused red dot where you wanted to be while you still remember.
2) Open your other eye when using your straight-through finder. By using both eyes, you can see where you're going with your free eye in open space at 1:1, and as you approach your target (while slewing) you can see that target start to converge with the magnified version through your other eye. As they merge it becomes very obvious.
So - both methods work for me.
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