Current way is indeed not optimal. Maybe it would be better if a little text file fetched at download startup did hold versioning information for essential tools. That way, version changes of e. g. SigCheck only need to be put into the file on the server, and all installations get the hint at next download run.
For the die-hards, SigCheck 2.30 could be kept as a separate filename, although, the old SigCheck versions might stop working soon, anyway.