Answer: You can plant in October or in February and your peppers should thrive. A 28 inch long container will support 3-4 dwarf pepper plants but I hope the planter is 5" wide, not 5" deep. The roots will need much more than 5" of soil depth in order to grow well. If the container is at least 10 inches deep your pepper plants should thrive. A self watering container is just fine. It will provide just the right amount of moisture for the roots of your plants.
Q&A Library Searching Tips