Then it looks like you want a version of the no autonomous raking hack where you don't want your Sim to rake if there's leaves on the lot, but when you tell them to rake, you want them to continuously rake until all leaves are nice, piles of leaves or until you want them to stop.
I like watching my Sims rake because they don't do it often. The advertisement is extremely low that the leaves will stay on the ground for days. Then all of a sudden, one of my Sims wants to rake and I'm all giddy.
However, when they rake, they'll continuously rake until every single pile of leaves has been raked and their temp gauge is all the way in the red and their energy is nearly zapped. But then again, I have a slow motive decay hack, one of those hacks that stops spontaneous combustion, and I normally just let them do whatever they want.