I haven't done any assembly on intel chips. The Motorola 68k was so much easier to program I never even looked at anything else. I guess that has improved by now?
Chips are more complex, more features etc. Things pile up for compatibility. That is a good and a bad thing.
As for an ISA, it's not clean but there's only so much you can do to an assembler language, so it's not that bad. And the docs are pretty good.
(If you're following Paul Carter's book above, use something that supports protected mode, like a 386.)
The Genesis port ran on a 68k of course.
The TMS34010 was something like a CPU and 2D graphics processor combined. It has the ability to change its word size from anywhere between 1 and 32 bits with data addressable on bit boundaries. It's wild.