> The II was a dead end. The 65816 was not a nice ISA to program for.
I mean you make this statement like its some kind of technical roadblock. Which might have seemed appropriate in the early 1980's but with a bit of digging would have been understood to be false.
There have been various proposals for 32-bit 65816's, and it wouldn't have been any different than any of the other architectural extensions done to other processors (never mind the conversion from 6502->65816). Modal decoders (ex: Arm), prefix bytes (ex: amd64), virtual execution modes (ex: vm86/i386), etc all provide a method for building a new architecture while maintaining backwards compatibility with the old.
This stuff is an economic or business decision. At Apple apparently it was a political/business decision, rather than anything technical. They could have (as the IIGS proved) just have created an mac like experience on the apple ][ line, while maintaining software compatibility. None of it would have been "pretty", but that is almost always the costs associated with evolving a technology stack. It took roughly a decade to evolve linux from a UP kernel to a SMP one without the BKL. In that time, and some of the results weren't what anyone would call pretty.