I suppose you are asking about pelargoniums?

Yes, you can make more than one cutting from one stem, but my experience is that the more the stem is "wooded" the harder it find it to make roots. And is might be wooded from just one season.
Try!

I don't think it is science when people wait with planting the stem so there is no right or wrong. If you wait one hour
and it makes new roots, well, then one hour was the right answer ;-)

But some free advices. Put the stems along the rim of the pot, and yes, you might put more then one in each pot to save space. Water the dish under insted of the earth within, and if possible, mix in some vermiculit or other such component in the earth. Keep it light while rooting, preferable from under the pot.

Good luck :-)

To keep the pot with cuttings with light from under is very difficult ... try heating instead :8)