You can’t use Insight for writing the flash regions, as the GDB protocol doesn’t know about different types of memory yet. Use the OpenOCD’s “flash” commands instead (see http://openfacts.berlios.de/index-en.ph … D_commands for a list of commands). You can enter these commands either via telnet or via GDB’s “monitor” facility.
The OpenOCD also expects a plain binary for flashing, but you seem to be trying to write an ELF image. It depends on your toolchain how you’re generating the plain binary, on a GNU toolchain you’d use “objcopy -O binary source.elf output.bin”.