I would still request the ocean/pool view when you check in. If you're planning to spend a lot of time in the room, worth it, if not - I wouldn't bother.

What do you call dressy? It is not ultra casual at night, but I wouldn't call it dressy either. I did wear a dress or a skirt most nights (but I'm not a real casual person anyway) and my husband wore chinos and sport shirt - we both felt comfortably dressed.

People in town do dress up more - no shorts, etc. at night.