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Originally Posted by Crowmeister 
Do I need to upgrade the 1.5 firmware to do what I want to?
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This will help you with upgrading.
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If I do upgrade to Dark Alex's newest firmware do I get the benefits of Sony firmware (like the support of larger Memory Sticks and the support for other image files) and play homebrew's?
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Yes you will. Web Browser, Playstation 1 Emulation support, etc...