I think I can answer some of the questions. I haven't got either a Cortino or Maple (yet), but I have been doing some investigation on Cortex-M3 boards.
A Cortino and a LeafLab Maple both use members of the same ST Micro Cortex-M3 STM32F103 family of chips. There are differences between the number and type of peripherals across members of that family of parts, but both Cortino and Maple have a version with the same STM32F103RB, which is 128K Flash program memory, and 20K RAM, and the same peripherals in a 64-pin package (so lots of I/O).
The same compilation and link tool chain will work for both.
GNUs' gcc for ARM is freely available as Open Source, and you can get it from GNU, or from codesorcery.com who offer commercial support and an IDE.
There are tutorials for installing this toolchain on various systems. Pete Harrison at micromouseonline.com gives links and an explanation of how he did it for Mac OS X, but I'd suggest starting with LeafLabs packaging of their work in their version of the Arduino IDE.
An obstacle is the upload to the bootloader, all the rest of the toolchain should work.
AFAIK, the LeafLabs folks are using a vanilla gcc (but I'll try to report back if I discover otherwise).
'Out of the packet', i.e. 'raw' as it comes from the manufacturer, the STM32F103 does have a boot loader already installed on chip, but it boots from a serial USART. Maybe that is why the Cortino folks appear to use an FTDI USB to serial chip on their board, even though the STM32F103 has on onboard USB. The LeafLab Maple uses the on-board USB support in the STM32F103; AFAIK, that is the major difference between the two boards.
Other versions of the STM32F range, specifically STM32F105's have a USB bootloader on chip 'raw'. That '105 bootloader looks like a USB DFU device. USB DFU is a 'standard' (like HID, Mass storage, CDC serial etc.), specifically designed for updating firmware on devices, and many Operating systems have DFU drivers already. As an example of a device which uses DFU to update is the iPhone. AFAIK, Windows doesn't support DFU properly (I am not a regular Windows user, so I'll leave it at that).
The Maple folks have written a bootloader for the STM32F103 on the Maple. It may be possible to get this working on a Cortino, but I couldn't comment on how easy or difficult that might be. Also, a Cortino is almost $10 more than the equivalent Maple ...
AFAIK, the only way to get the Bootloader into a 'raw' STM32F103 is programming it via JTAG (similar to burning the Arduino bootloader into a 'raw' ATmega, but JTAG is usually much more expensive than an AVR SPI programmer), or via the built in bootloader which uses the serial USART. So you could probably put a Maple bootloader onto a 'raw' STM32F103 that way. Pete Harrisons blogs talk about how he did it, but he used a low-cost JTAG.
HTH
GB-)