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Olly is handy for processes that are running where you also need to look which memory is used by what, so handy for packed programs and so on. Windbg is usefull for drivers and other such stuff. ida is awesome for understanding the codelogic and the disassembly, the debugger is fine too. ida can handle pocket pc exe's, linux exe's and images of various other kinds where other debuggers simply give up.. So ida is a must have for strange platforms (for example nds and so). But for strange platforms there is also codewarrior but disasembly with that and trying to understand what goes on is harder with that. I only tried it once or twice or so, likely it is way better now...
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