Thank you @zerojay ! This is tremendous. Very easy to install, and after a minor issue with the vgm directory permissions, was able to get everything up and running....kind of.

Few issues below. Any help would be much appreciated.
*Update Recreating the autostart.sh file fixed issues 1 and 2.

Both the playmusic.sh and generatem3u.sh scripts are running without issue, but music will not start automatically after boot. I can start it by running the playmusic.sh script from the command line (or via ssh), but it only plays through HDMI port. I don't see anyplace in the vgmplay config file to point it to the Headphone output on RPI4. The playlist does not loop. Playback terminates after reaching the last item in the m3u file.

@phane Thanks for the tip, now it's working properly!

12 months later, nearly, and it seems that my memory has grown fuzzy over the last 35 years.

Whilst I remember, and played Total Eclipse (and it looked like a promising contender), and Marble Madness was fun, but as far as I remember, no prize, it was neither that I was thinking of, and I got the prize wrong.

The game I had in mind was Gyron, which had a prize of a Porsche 924 or £12,500 cash for the first to complete.

I'm so happy to have finally cleared up this mystery. :)

Somebody needs some deleted.....

@brandflake11 LOL you beat me to it

@prop When I think of a retro pc game where you jetpack around, Halloween Harry comes to mind (aka Alien Carnage). Though you are not running from police. It's also DOS, not Win98.

@ebeyer
In that case, i'd keep an eye on GOG, they often give away free games that use SCUMMVM or DOSBOX, which can be played on retropie. (They're licensed to sell the games they're selling)

Speaking of SCUMMVM and DOSBOX these platforms also have hundreds of freeware titles available.
https://wiki.scummvm.org/index.php/Where_to_get_the_games

Furthermore, you might want to look into some homebrew for the various systems.

And lastly although not free, fanatical.com which is is also a licensed storefront often has the entire Sega collection on sale for roughly 5 bucks.

@rkoster
Good point, I agree with you, we will stay with consoles. That was the first idea behind that survey/challenge.

@crusadeklr I'm not sure I understand. What's wrong with using the in-game save feature? In game saves should work just fine.

Shoot, well I dug a little deeper into the KLOV site, and it looks like there are some reviews on there after all (not many tho, and several games simply aren't reviewed at all). But PlayRetroGames.com and Adb.arcadeitalia.net seem to be other sites that have some occasional reviews (as well as IMDB itself, since let's face it, some actors are now appearing in video games). So I feel bad about the massive list, but I may leave it up for a bit, just in case anyone here is at all familiar with any of those games, who knows...

@pierpa86 The link is not working , file has been canceled

@MortalWombat - The cores that compile in a "reasonable" time frame (under 2 hours) are mame2000, mame2003, mame2003-plus, mame2010 and FBNeo. mame2003 (plus changes ported over), mame2003-plus and FBNeo seem to be under rolling development. I watch those cores as new games and fixes are being added all the time.

Another way to run CD-i (cdimono1) with MAME standalone (like MESS without Lr)

go in /opt/retropie/configs/cdimono1
open your emulators.cfg

add:

mame-CD-i= "/opt/retropie/emulators/mame/mame -c -autoframeskip cdimono1 -cdrm %ROM%"

To set your "Input (general)" and "Input(this Machine), follow step 10 and 11 of this Tutorial.
Tutorial: Handheld and Plug & Play systems with MAME

You can use .chd without specific MAME naming and without dummy file.

@kounabi22
Meh...
I'll stick with a permanent preference for the PS2 version.
It's a game from 2000, yet the Graphics are The Tip of Everest!
Too bad PS2 Emulation is a train-wreck that's yet to be cleared up.