No, castrandom and castsequence do NOT support multiple [] target selections on multiple spells -- the above does not work (tested just now). You have to keep all your "target" logic at the beginning, you can't have any more one a spell name is in place. The original suggestion does work however, just having a "dropdown" condition. I would suggest something like:


#showtooltip
/castrandom [target=targettarget] Lightning Bolt, Lightning Bolt, Lightning Bolt,
/cast Lesser Healing Wave

(you can add/remove LBs depending on how often you want LHW tossed off, if you just have 1 LB theres a 50% chance LB will go off and a 50% chance LHW, with 3 LBs its 75/25).

Remember, [target=targettarget] is saying use target-of-target for this next cast. Its not an evaluation, its not a "do I have a target selected?" check, its just simply telling the cast what the target is. There is no way to make multiple targets off one single cast line as far as I know, since the evaluations all occur FIRST and then the spell being cast is selected. You can make the evaluations as complex as you want, but there is no way to choose multiple targets, you only have to use the drop-down logic of a "," which means "do nothing, don't eat the GCD and continue to next line".

You can make the macro even more fancy with things like:

#showtooltip
/castrandom [target=targettarget,nomod,harm] Lightning Bolt, Lightning Bolt, Lightning Bolt,
/cast [mod:shift] Lesser Healing Wave
/cast Lesser Healing Wave

this will LB tgt-of-tgt if no modifier is pressed and the target is an enemy. if shift is pressed it'll always cast LHW. If nothing is pressed and nothing is cast the first line (25% chance) then it'll drop all the way down and cast LHW as well -- this lets you force a LHW with a shift, and still gives you random LHWs.