For me...all the time. Sadly none of the game-creation software I have used have allowed me to do what I wanted to do. I've tried all the versions of RPG Maker...all of them lack something another version has. Which really sucks (and afaik, all of them lack the ability to make a spell that drains health from enemy and adds it to you).
What are you talking about, you just have to code an object somewhere with a variable for the health, have it set to a random amount, neg the damage then give it to your character.
Gamemaker requires some stupid workarounds (invisible controller objects), but it does make some things shorter to code, and the automatic save/load features are a fucking LIFESAVER.