Subsoiler Question
#3
Before tilling is how I've always done it. Unless you have a heavy 4wd tractor, getting traction in loose soil can be a problem. Either way you will need to till/disk afterward to prepare your seedbed before planting.
#6
Subsoiling does a lot of good for your soil, but depending on the way your plot drains, it may not fix your flooding problems. If the flooding is caused by the water that is falling that is not draining off or infiltrating your soil, then it will probably help. If the flooding is caused by water falling off-site running into your food plot and flooding it, then it probably won't help. In that case, you will need some kind of drainage or diversion constructed.