You guys sound like you are considering walking, but I can only ride, thanks to millions of jump shots and rebounds nobody tells you are going to destroy your knees in old age.
Living in Miami, seasons don't change enough to affect golf much. We get more rain during the summer, mostly in the afternoon, but I play in the mornings. What we get that affects how I play is wind.
During the fall, hurricane season, the wind comes off the ocean and it's fairly constant when it is there at all. It'll vary greatly, from a gentle breeze to 30-40 mph walls of wind you can lean into.
I'll rarely hit a full shot up high, because there's very little to indicate wind upstairs. I'll play a more European style, bumping the ball along the ground, usually with a 6 iron. If I need to clear some hazard, I'll hit 2-3 extra clubs and punch it onto a green. There's little need for carrying hazards that at Killian Greens, with bunkers to either side of the greens, but none in front. Where we have to clear lakes or canals, there's still plenty of space to land the ball and run it up.
During the spring, the wind usually comes in gusts from the west, off the Gulf coast, so I feel like it's the hardest time of the year to judge shots. At contact, a 30 mph wind can slam you off balance or affect the shot in the air. It's a lottery what happens then. I suppose I probably hit more bump and run shots then, than in the fall.
That's about as complicated as it gets for me.