GW only said do not upgrade your boat before the first mission. Other than that you can upgrade when you want.
The crew is getting experience. You have to award the medals in the crew recruiting screen. It it not done automatically. You are the captian so go award these medals.
Yes, GW has plenty of dead cargos in ports. There should be a few ships moving about.
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“You're painfully alive in a drugged and dying culture.”
― Richard Yates, Revolutionary Road
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