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I became interested in DreamCast development around year 2000 and taught myself the Hitachi SH-4 assembler. A friend of mine soldered a RS232 12V serial port to my DreamCast (The DreamCast has a 3.3V serial port available on its motherboard) and I used the Serial upload slave from Marcus Comstedt to test my code on the DreamCast.
At a point, I had contact with the Echelon DreamCast warez release group. This group had already released some cracktro, and I was interested in coding some for them.
My development machine was a Pentium 200MMX PC running windows 98 hooked to the DreamCast through a serial cable.
The toolchain was a version 2.95 gcc for sh4 running under Windows thanks to cygwin. I don't remember if there was a libc, but I avoided using it anyway, you'll see calls to custom dc_memset() dc_memcpy() etc.
I had Microsoft Visual C++ 6 installed on the machine and used it to build the PC tools.