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1. Would it be easier to work in Windows? I've seen some postings about problems getting a USB blaster working in Linux.
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If you are familiar with Linux, use Linux. Getting the USB Blaster to work isn't really a "problem", it is just that it is not done automatically for you by the installer and you may need to edit a configuration file or two.
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2. Would it be better to start with the DE2 or the BeMicro? My goal is learning and playing.
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Unfortunately, the older BeMicro SDK has an LPDDR external memory which you need a 3rd party IP core to use. This also isn't really a "problem" except it is probably a little more complication than you need starting out.
A big perk of the BeMicro is that it is laptop (couch) friendly.
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