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Dashes or underscores as in -1 and _2 are probably OK with most SEs, but I'm SURE text is OK everywhere. I'd avoid any other punctuation characters though.
I normaly put all images under \images, I put Java script under JS and so on. On all images I make use of ALT tags by using keywords (I have been told it does not carry very much weight anymore but every bit helps IMHO), I make sure that the ALT tags on a page are not just the same phrase over and over. I make sure they are non repeating. On picture names I use keywords again like mensrings-comfort.jpg.
I never thought about pop ups.
Just my 2 cents,
My pages are produced offline from a DB and automatically named with 1,2,3 etc at the end, soon I will have alot of pages but would one,two,three etc be safer ?
I am sure this could be an issue for others so I'll try to complete this thread but any help would be much appreciated.