I spent a bunch of time gardening in the PNW, which pretty much rains 8 months of the year through the winter. My soils were mostly pretty dense and slow-draining. Some thoughts:
Raised beds or gentle slopes are good, anything that can let the water run off and oxygen enter the soil.
A lot of overwintering plants got black spots on their older leaves, or the older leaves go yellow and thin and sort of dissolve/sludge off. This didn’t seem to hurt the plants at all, and happened with everything from brassicas to blackberries-- the same blackberry plant would then go on to completely engulf a house or a tree the next summer, so it definitely wasn’t necessarily a problem. Signs that I’d read as a problem are things like the whole plant going pale, the leaves feeling less turgid, and the new leaves (which often stall out at this time of year) getting signs of damage. Also if you rock the plant gently is it firmly anchored in the ground, or does it feel loose? All of those indicate root issues from soggy ground and would be a significant signal to me. Covering the plants, like with a hoophouse, will reduce the spots, but I bet selection could handle this too.
Bananas were wrapped, piled up with a layer of straw and then plasticked, which sometimes made them rot but was supposed to protect them from freeze/thaw. Some plants accept freeze/thaw a lot better than others and I guess bananas had issues with it.
Bigger hoophouses entailed a lot of work (watering, especially if waterlines were going to freeze/thaw) but I always kinda wanted to just run rain collection from a house gutter straight into a hoophouse, no collection container, and see how that did. Not sure if enough water would make its way through the soil for smaller hoophouses.
I always covered my tomatoes to avoid blights; they definitely went downhill as soon as the rains began. It sounds like folks are working on selecting around that issue though.
Assuming your soil isn’t extremely free-draining, anything dug into a hole (like an apple tree, or if you dig out a hole to put compost in for squash) and then you fill the hole with nice soil, all the airspaces in that nice soil will fill up with water and the hole will basically be an invisible, plant-drowning puddle. If you have that kind of soil (I think yours was sand, so this doesn’t apply) then try to bare-root anything as much as possible when it’s planted, so there’s no big difference in soil around the roots.
Beware areas of impermeable surface, like eaves and pavement and patios: they discharge a lot of water, and so avoid planting things that can’t tolerate soggy soil in their discharge areas.
Swales are magic. Plant on top, the roots have space to gather oxygen at the top of the swale, and then in the summer can follow the collected water slowly down deep into the soil.