I don't see why you couldn't simply copy the install dir to your pen drive then just run the exe from it. Only thing that might hold you back would be if it needs a reg entry. I don't see why it would be illegal but my gut tells me it is probably a violation of the EULA.
whats it got that a regular pen drive doesnt have??? as for registry entires, couldnt you just simple save the photoshop registry entires into a registy file, then double click add thoes registry entries onto said comp and open up photoshop.
I have GIMP portable on my USB drive as well as portable open office, portable firefox, and portable Thunderbird to name a few. GIMP is actually quite a nice program these days.
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