the easiest/cheapest usually refers to not bothering with an entry level mates license (200/500), but rather wait until one has enough time for a limited (500/1600) masters license. That way in many cases you only have to “do it once.” No special licenses for Alaska. The towing done here is usually complex and experience from other trades don’t cut it, the more difficult to get a license, the better. The system has many flaws, no doubt though. Particularly OSV licenses. Fault there lies with the bosses, not Mariners.
I recommended leadership and managerial skills so he’d only have to “do it once” since I was suggesting 500-master.