You might find the Parallax Propeller 2 interesting.
The earlier chip had that retro feel in the ways you describe, but it was just a bit small for computing.
The current one is pretty nice!
It is an 8 core multiprocessor. That may seem complex, but the way the cores are implemented is clever and generally useful without an OS though some are in development.
Each 250+ Mhz core has 2K private RAM, locally addressable by the core, and another 2K LUT lookup table RAM that can also hold code.
The system has 512Kb shared RAM that all cores have access to and that they can run code out of as well as manipulate data.
Here's the cool stuff:
Each core has a data streamer capable of many signals, display from old school NTSC through VGA AND HDMI. Audio, many other streamer modes and uses are available. One per core! It has a color transform engine meaning one can drive a TV with one, VGA with another, HDMI with another and have the colors all make sense from single or multiple display buffers.
This is all software driven and simple, meaning displays can be any mix of tiles, sprites, bitmaps, whatever.
All 64 pins have a smart pin state machine for measuring signals, other pins, and each pin has 8 bit ADC, DAC capability as well as simple digital mode signaling.
It can boot from a program on SD card, over serial, from eeprom.
Currently, there is a dev environment able to mix and match, SPIN, BASIC and C.
Again, each core runs independently. One can do crazy stuff like run an oscillosope on one core to display the signal output of another one, or an incoming signal from off chip.
Or, have one core emulate a CPU, while the others do hardware, video, sound chips.
In my view, it is a nice, robust system on chip. Definitely one person understandable, and if one wants an OS, write or use one of the ones in progress.
Or, just write simple programs and load up drivers onto the other cores to display, work with USB, serial, drive motors, whatever.
There is a Forth self hosted environment and others are being made.
I have enjoyed these devices for a while now and they are one of the closest things to older 8 bit systems around.
These are 32 bit systems and there are a lot of features I did not mention.