No, TipTop won't do everything the OP wants. Sounds like he wants a whole tooltip overhaul.
@Vinoue: The further you get from the default tooltip, the more likely you may run into a problem with MyRoleplay. But it doesn't hurt to try two addons together to see if they're compatible.
To do all you want, try one of these addons instead of mine:
http://www.wowinterface.com/download...93-TipTac.html
http://www.curse.com/addons/wow/cowtip_luatext
(The first may work with MyRoleplay, but I'm not so sure about the second.)