I do the same thing! Jawline up first then dry the upper face to allow you to stretch the stubble up so you can get to it.
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My guess is you are taking on too much too soon. You need more facility with the razor which you don't have and that is why you are struggling with these more advanced areas. it will all come with time.
I actually learnt to straight shave (properly? or better?) by watching "Jockeys version 3" on Youtube:
Straight Shaving Tutorial v3.0 Part 1 - YouTube
I wasn't at all sure how to do the point of my chin or the bit directly underneath without unleashing a stream of claret until I tried Jockeys technique.