Q1: Not sure what you mean by this...
Q2: If by experience you mean reknown (which you purchase upgrades with in base) then this is tonnage related. Sinking destroyers won't net you much, but sinking battleships will. Just like sinking small merchants wont get you much but sinking T3 Tankers will.
If by experience you mean your crew's experience, then I'm not totally sure if it relates at all to the size of the target sunk, or just the fact you sunk one. Your crew gains experience by being used for their jobs, not just from sinking ships. Experts feel free to jump in here.
Q3: You can purchase crew with special abilities in port, and I have had existing crew develop special abilities on their own, but did not manifest their abilities until I got back to port. Note that special abilites do stack.
Q4: If you are driving a uboat, I find off Fremantle to be really great, seems like endless King George BB's there to sink. Not every convoy there has them, but a lot do.
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