I think it helps greatly if we know that Shmi is no longer a slave. As difficult as it is for Anakin to try to forget about her, it’s more palatable if he knows she is free. I’d have this done in TPM and she is left behind because the Jedi don’t make allowances for parents tagging along. Qui-Gon gives a disapproving look and Shmi gets it and says, “my place is here. My future is here. It is time for you to let go.”
In AOTC I’d leave it implied that Anakin went back at least once, knows the Lars and plausibly had a conversation in years past with Owen about staying. So we would cut Watto in this telling.
I think the story is stronger if Anakin simply can’t let go of his mother even when she is relatively safe. Adopting Peter Pan’s idea to make it more explicitly the Jedi’s fault helps too. Especially with all of Anakin’s ranting about Obi-Wan holding him back which feels out of left field in the movie as is.
I don’t know if it might be cut so the line, “Mind your thoughts, Anakin, they betray you. You’ve made a commitment to the Jedi order…” applies to his dreams about his mother.
Today I played around with the scene you suggested and frankenbit something together, as Eddie would say. 😉
Its not perfect, I don’t particularly like the specific wording of the line I came up with, but I think this gets the idea across.https://drive.google.com/file/d/17C_nZGiBtV2jcEP5i1e0jCEQ4uqb13gS/view?usp=sharing
Good thought having it play in the background, it does seem to be a tough section to cut visually given how they continue walking through.