This is really a complicated subjects, there are so many choices and trade-offs.
With respect to hardware I would go for a low-end micro-controller, because things tend to become easier when they become smaller, and the farther away from the desktop the more you learn the mindset of embedded programming.
Since you are in Japan it is probably best to check locally what controller is popular, so you get good community support and can easily buy parts.
Here in Germany it is AVR ATMEGA, and I think it is a good choice. It has the best support by GNU tools, it is available in DIP packages and can run off its internal oscillator so it can easily be run on a breadboard. The biggest hurdle was that I needed an ISP programmer. There is a good tutorial in German.
I also have an R8C by Renesas, which might be more popular in Japan. It is harder to get the GNU tools running, I had to build them myself from source. For MS-Windows there is the free IAR Kickstart suite with code size limited to 4KB. It can be programmed with a serial interface (but with TTL levels), I got a FTDI USB-to-Serial module for that.
As for RTOS, take a look at OSEK, there are several free implementations.
It can be used on very small controllers.
You could also write a basic RTOS yourself, it is not that difficult and you learn the most.