The # series is the shutter count up to units of 10,000, while the $$$ is sets of 10,000 images. Then the shutter count is the number assigned to the latest image shot when you see it on your camera viewfinder. have not low level formatted your cards and reset the numbering have not used other cards from different cameras with images on them, One possible thing is, if you have left the counting system at its default i.e. Certainly, all of the documentation I have read on the subject indicates what I have have said. Now, I use Windows and apparently some people claim success with a Mac OS, but I can't verify that.
There are many 3rd party apps out there but I have not found one that works.