I have used both IAR and Keil tools for several processors, both are good although I do prefer Keil.
I use the Keil ARM7, ARM9, ARM Cortex compiler. Their processor and peripheral simulator is excellent, and so to is their debugging support. The peripheral simulation and debugging facilities make the license worth paying for. (I've not used the IAR Arm tool so can't say what its debugger and simulator if any are like.)
The GCC compiler may or may not be good (from what I have seen it is not a patch on the ARM Real-Vie compiler) but without the processor and peripheral simulation that you get with the Keil tools you only have half a tool set. Since I write software for a living, that would make a ?free? compiler a very expensive option indeed.
As for licenses, I have had a system disk failure and a separate mother board failure this year, Keil reset my node lock license without difficulty both times.
After having tried two tool that were supposed to work under Cygwin one tool I had two one hour sessions with one of their develops trying to get it to work on my PC, the other about 45 minutes with their supposed expert. Neither tool ever did work and as a result of the damage done to my PC by one of the ?Cygwin expert? I had to reformat my PC to get ordinary windows applications to work again. I think at least some of the problems were they expected me to run with no firewall and no antivirus, because their tools were not compatible with these !
I did look at using Linux on a major development for a piece of laboratory equipment, but ended up being frightened off by the enormous costs of a supposedly free platform, and all the extra add on licenses I needed to buy. I instead used WinCE ? fantastic $3 (£3) a license, a few hundred pounds for Visual Studio and your there. Actually I did need platform builder too as I tailored the OS for our hardware, but for under a grand I was away, and the end user was able to test the user interface on a standard HP PDA ? brilliant. Oh and other than Visual Studio you don?t need to buy anything until you?re ready to ship to paying customers. Being able to run the software on a standard PDA was fantastic especially as the hardware was designed in the UK and the Japanese version was targeted at Japan. I even used developers in the USA, and the Ukraine as subcontractors with them not requiring the target hardware. The salesmen also love carrying a demo of the unit on a PDA in their pocket. I guess many will turn their nose up at WinCE but if its right for your application then doing so is foolish.
Regards
Eric