Rebasing to get a "clean" history is overrated. The best way if you want to preserve history is just to do the merge instead of a rebase. That way if you ever need to go back to a revision, it is exactly the same as the one you tested during development. That also solves your issue about the previously solved merge conflicts.
If you don't care about preserving history, you can create a new branch off of master, check it out, then do a git read-tree -u -m dev to update your working tree to match the dev branch. Then you can commit everything into one big commit and merge it into master as normal.
git merge --squash is now my preferred way of rebasing after a large amount of work and many merges (see this answer). If the branch you're working on is called my-branch and you want to rebase from main then just do the following:
Regarding the replay of merge conflicts, you can use git rerere to maintain a database of how merge conflicts have already been solved, so that performing a rebase that results in the same conflicts will have the laborious parts done for you automatically.
The one thing to look out for is that if you resolved something incorrectly it will be automatically borked for you next time too, and you may not really realize it.