1) I like stockingfoots - they dry out faster than boot foots.
2) Downside of stockingfoots is that sand gets into your boot. Every few hours you have to empty them. I think you can get special thingamabobs that wrap around the gap between the boot and the waders to prevent this.
3) I haven't seen a breathable (low, medium, or high-end) that won't eventually spring a leak. Hodgman, Orvis, Cabelas Private Label, and Simms Gore-Tex Guideweight as well as Patagonia have all leaked. So if you fish hard, buy more than one pair, and ask the retailer what the leak repair policy is.
4) Get a pair of neoprenes for late fall.
-WW
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