There were similar ideas in past, but as I know nothing is made. Maybe just because it is not hard to navigate in Desktop, and launch some game quickly.
AUTO run may be not good idea, however - then you loose GEM, AES , so need to make a lot of things self if want some better looking user interface. Plus, there are games which can not run from AUTO folder - those using AES calls - like Deja Vu .
Scanning all partitions for executable files may take some time at every boot, what may be decreased if games are in specific directories only. Still, if there is for instance 700 game, it will take at least 1-2 minutes, I guess. Since you want some extra data (game infos and pictures), as best idea seems to not scan after boot, but making some database, which will be updated when adding new titles. Things can be made simpler with tool which will fill database by scanning target directories (but not at every boot), so you will have file locations and names, and can launch games. Adding extra data is optional, and can be done any time.
I don't see that this must be written in 68000 ASM, at least bigger part can be done even with some basic compiler.
Actually, I made something like it in 2008, pretty simple. User must compose list file, containing paths to executables. It was made mostly for games requiring AUTO run, which can not work well when running from Desktop - so no need for some Boot manager and similar. In attachment is source too.
In case of PP hard disk fixes and running under Steem - a lot needs Pasti hard disk emulation in Steem - will not work from some partition 'created' by Steem Disk manager. So, you may need image file with autoboot hard disk driver too.
Program takes not any RAM when starting game - it loads executable to same location where self starts.
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Famous Schrodinger's cat hypothetical experiment says that cat is dead or alive until we open box and see condition of poor animal, which deserved better logic. Cat is always in some certain state - regardless from is observer able or not to see what the state is.