I don't think anybody fills much slower than I do (over 3 hours). I still get a fair amount of pressure drop after they cool. I have my compressor shut down at 3800 LB and the tanks drop to 35-3600. I generally don't wet fill but when I do it makes a difference.
300psi drop? Sounds legit. I would say that's acceptable. Overfill your desired pressure and let it settle.
That would be really really slow. I take 30 or 40 minutes to fill an hp 100. That still builds enough heat in the steel to lose around 300 psi after the tanks cool, which I later top off. Way easier to me than a tank bath but I have the convenience of 4 whips and a cascade.
Same as above.