Ahoy and welcome, jangles!
In answer to one of your questions, you can play multiple careers either with or without SH3 Commander, altho most people here will probably agree that Commander is a must-have addition to the SH3 experience.
You can't "play" multiple boats at the same time, since when you are in the game you are commanding one specific boat and that's it. However there's nothing stopping you from having several active careers at the same time and playing whichever one appeals to you at the moment.
The advantage of Commander is that it allows you way more control over starting and managing your career and crew.
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