I lived it being a problem with the NES to SNES as my parents were deadset against me wasting my "money earned over the Summer cutting grass" on it if it didn't play the old games too. Personally, I was with Nintendo on it - I kept my NES plugged in as well as my new SNES. Just I didn't play my NES as much, but when releases were few and far between early on (I was a day one buyer of the SNES, had one on pre-order/lay away with Walmart). I remember loading up Final Fight and loving every second of it, I didn't care that it was slimmed down a bit for the SNES. It was fun.
I remember the Master Gear Converter for the Game Gear, it was official and it was pretty neat. It only allowed playing cart games, no card games, though. Sega also released a TV tuner for the Game Gear. Man, back in the day, living with only over the air channels, I wanted that so bad.
I could understand not offering a Power Base Converter style adapter for the Dreamcast to play Saturn games but I agree, they REALLY needed the PBC with Genesis support for the Saturn. Had they had that at day one, when they announced it was launching 6 months early, maybe history would have been slightly different. It certainly would have helped make the Saturn the 32-Bit platform to own.
Imagine if they did the PBC with Genesis support and offered CD's with CD remixed audio for certain games like Streets of Rage. Would have been amazing, I think.
Sega missed a lot of opportunities. I think the fame of the Genesis went to their heads, honestly.
RE: Where Sega Started to Fail or How the Master System Might Have Saved the Sega Dreamcast