Any way to get multiple abilities on the same key?

[Niwashi]

To make this possible, the easiest way is to make macros accept logic gates. What that would entail however, would be the ability for people to start legitimately botting without a 3rd party program - because "if"/"while"/"for"/"else"/"etc" is exactly what is necessary to write working software (bots). It is possible to write a program (game in this case) that lets you write "Scripts" (kinda like macros needed to make your idea work) that you can manually program, but I think some very fundamental rules in the game will have to be changed for this to be a good idea.

They could add conditionals without adding loops. They could even specify what types of conditions those conditional statements can use. They did it with FFXII's gambit system, and if they wanted to they could implement something similar here with macros. That wouldn't go as far as allowing full-fledged botting. It would, however, make macros a lot more powerful than they currently are, and that's something they're trying to avoid. (They're afraid if macros are too powerful, they'd become de facto required.)

[Niwashi]

There are certain limited situations where you can make a macro do either of several different actions, but only if some of those actions are unavailable. You can, for instance, create a macro that says to cast an attack skill on your target unless your target is a friendly player who you cannot attack, in which case cast it on their target instead. (Healers use this a lot so they can keep the tank targeted while they alternate between healing him and attacking the enemy he's attacking.) Or you could make a macro to use a particular skill unless that skill has been lost to the level-sync in which case use a lower level version.

But there's no specifying of the conditions under which you'll switch. The condition is always to do the first skill unless it's unavailable, in which case do the next unless it too is unavailable, in which case move on to the one after it, and so on. (And the only reason it doesn't execute several is that the first available one will make your character too busy to succeed when attempting the remainder.) There's no way to specify something else like "If I have trait X" or "if my target has status Y" or whatever.