StartMenu: In Beta, standard start menu items would not possition below custom items. Some change on SOE's end had them always starting in the top left corner, which would overlay custom buttons. I reported the problem so maybe they snuck a fix into the final release. Never bothered to test it on live since placing the custom buttons below worked.
Incompatable Windows: all windows included in 9.5 should be fine. Not sure why it would work for you one day and not the next. I suggest reinstalling 9.5. Be sure to extract it directly to the Everquest II directory and not to the UI directory (A common mistake).
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