I have mild winters. I don't have a lot of room in the garden and I try not to keep long term plants in there. I already have a couple that are taking way too much space as it is. Peppers do well in pots for about 4 years. I have some that are 8 years old in pots, 10 years old in the ground. I prefer to grow them in pots because I have a lot of varieties and I need to be able to move the pots as they grow so they will be spaced better. Some peppers do not last the year like bell peppers, but the hot and super hots can last a few years. If the pots are big enough, 4-18 gallons, the peppers can live for years.
Happy gardening in Hawaii. Gardens are where people grow.