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Depending on your budget, wants, and needs, a pool enclosure can be a worthwhile investment. It all comes down to how much you use your pool, and what it would mean to you to have year-round access to it.

If you know that you'll swim in your pool a lot, then having an enclosure means you don't have to worry about the weather. It's also a lot easier to maintain the water, because you don't have to deal with leaves falling into the pool, and the water's chemical levels tend to be more stable.

Yes, with proper heating or cooling systems and energy-efficient glazing.

A retaining wall can only function as a fence if it’s high enough on all sides to prevent someone from accidentally falling into the pool. However, most retaining walls retain dirt, which means their purpose is not related to safety. There would need to be nothing on the other side of the wall for it to be considered a fence, but in that case, it wouldn’t retain anything and would cease to be a retaining wall.  

Each state has its own regulations about pool fences, and laws to protect both swimmers and pool owners. Before installing a pool, you’ll need to research what the pool laws in your state, city, and county are to ensure that you’re adhering to the legal regulations. Inground pools typically need to have a fence around the entirety of them, but the rules regarding above-ground pools are less stringent. A good rule of thumb is to always have a fence around your pool to ensure safety for all.