Your Philodendron is naturally a vining or trailing plant and requires a lot of staking if you try to keep it upright. Tip cuttings with 3 or 4 leaves and one bare node at the base of the stem are the best candidates to root in either damp potting mix or water. You could probably insert the cutting in the base of the existing pot if you want. This is a tropical plants so it doesn't matter what season it is when you propagate it.
The red section is the sheath that covers a new leaf that is about to emerge.
