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I like to wait til the leaves reach the outside of the cup, or if you have holes on the side or bottom of the cup, look for roots. If you see some roots when you look through the drainage area then you definitely need to transplant
I've always waited until my root system is established enough to hold the soil together. I use the red plastic party cups that make it easy to slide the root balls out to check development. After doing this a time or two you can tell just by looking at the plant when it's ready.
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