Many chillies are native to Mexico; think about conditions there.
Sweet peppers need more water. My rule of thumb is, if put your index finger into the soil, to the second joint, and it comes out dry, you need to water.
I overwinter 1 plant for 1 year because, although they produce less fruit in subsequent years, they produce earlier.
When the first year peppers fruit, I thank the overwintered plant, and let it go to plant heaven, as it's often not so good then.