at first, watering was the hardest part. figuring out just the right amount. then i realized.. i can water and just drain them. i think taplas post in other forum mentioned about tilting the container at an angle and it will drain the water. also putting some sort of "wick" to have the water flow through the bottom.
on smaller containers, i usually tilt the pot at about 45 angle after watering. that seems to drain most of standing water. on larger containers, i just stuck paracord in the bottom. but with larger container, it's hot enough here that they need to sit on water most of the day.
cuttings in cup is little tricky. that's why i use peat pot. if it's really dry, the peat pot inside of the cup will turn light colour and weight's almost nothing. that's when i water them.. when the peat pot turns khaki or the cup is really really light.. whichever comes first. and i keep them out of rain.
pete