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I'm wondering why a "6-pack" OUPV license (for which you need only a year's time of 8-hour days) wouldn't serve your purpose while you continue to get the rest of your time for an "inspected vessel" license such as the 50 or 100-ton Master of auxiliary sail (and steam and motor).

And if you're going to carry more than 6 paying passengers, you will also need to be doing it on a Coast Guard-inspected vessel, meaning a lot of design and building requirements (under 46CFR subchapter "T") which your dream catamaran may not have.

Counting time? I had to add in the rowing time going out to the mooring and back to get enough, but they accepted it. This was 30-odd years ago, though.
 

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yeah and that's where STCW kicks in as well, at 200 tons. Why 100 tons is great for us desk-jockeys and rag sailors or occasional fill-in mate or second captains on the larger (99 gross ton) crewboats aka dive boats.

Anyway, way back when I was a Coast Guard marine inspector, the jingle was, "you can drown six--you can't drown seven". Both humans and boats need bigger certification for seven-plus.

Plus I'm not sure a lot of sail charter operators (meaning individuals with their own boat, not larger companies) really want more than 6 passengers at a time, nor do they want the expense and regulation of a COI. So I'm wondering if OP couldn't make do with a 6-pack while working and gathering time for something bigger, whether license, certificated boat, either, both.
 

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Yeah, passing the physical exam is much more reviewed and picked over than before. You can thank the fairly recent COSCO BUSAN bridge allision in SF and the Staten Island Ferry casualties for embarrassing the Coast Guard into tightening up their medical standards and review, particularly as to prescription medications.

It's all in Here:

http://www.uscg.mil/hq/cg5/nvic/pdf/2008/NVIC 04-08 CH 1 with Enclosures 20130607.pdf

And the medications they hate are in Enclosure 4. Opioids and benzodiazepans a no-no. You need a good, and patient doc to trudge through the Physical exam form with you. I make two physical exam appointments: the first for the exam, the second to fill out the form.
 
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