Well here's what I do,
1. I don't think a little bit of water freezing in the tank would cause damage, unless anyone has other experience? But it's surely better to dry if you can, so:
I dry my tank out by lifting the front of the trailer, sponge and towel, then (with boat level again) leave hatches off all three buoyancy compartments (Bre) to allow them to dry out. I take any ropes etc out that could hold moisture and leave them in the cockpit which is under a cover.
2. see 1 !
3. I put the trailer on blocks to save the wheel bearings, the tires need replaced due to wear rather than rubber degradation this year. I suppose it depends on your mileage!
4. I've never yet had a problem with deforming boat rollers so don't jack the boat up. In fact this summer i sprayed silicon grease into the ends of the rollers and my boat comes off the trailer like a rocket!