Hey, Jethro - good job on the talk with your W. I totally understand how you feel about trusting her, especially if she thinks just saying she'd never put herself through that is enough. I love the having-a-baby analogy. We (and I'm including you guys in there, too!!!) do "forget," and if we don't change our beliefs and behaviors, we are SO likely to fall back into old habits.
But, some if it you have to leave up to her to discover. In terms of understanding how she puts herself in places where boundaries can get blurred. BUT, do not stop letting her know, in your best DBing ways, the things she does that worry you. Sounds like you're doing that pretty well, and maybe need to do it a little more often?
Squeaky wheel?
How to be a squeaky wheel and not a nag...haven't quite figured that out. Maybe it's not so bad to nag for what you need sometimes....