.esm files always load before .esp files, regardless of file modification date. therefore they should always be considered bashable, even if their file modification date is greater than a mergeable .esp file that has it as a master. Moreover, it should be bashable if its modification date is greater than the bashed patch being built.
However, this should be a low-priority task since BOSS automatically fixes the problem.
Rather than messing with all that, it sounds like Bash should instead simply enforce esms being dated before esps.