How do you do the untangling? I have been using an after-hook call to org-babel-tangle, which works quite well. It is a bit slow for large files with many code segments (like my Emacs init file at
https://github.com/zzamboni/dot-emacs/blob/master/init.org), and it requires a bit of discipline for editing only the org file and not the output file, but works well otherwise. I have never tried to de-tangle, that would require some markers in the output file I guess?
Here’s the code I use at the moment I am super happy with it, as it prevents my output files to get out of sync from the org file: