One of the things I find annoying is to hit a macro and then have to click through a series of questions. e.g. is this a sneak attack; are you flanking; is this your primary, offhand or both hands; is there any additional bonus to hit / damage; etc. A single popup with all the conditions you need to set would be awesome. It would be even better if the popup remembered your last set of conditions and came up with that already configured. You could also have shortcut buttons that configure the conditions to common presets.
