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Crew up with the pirates you want to go with first, then initiate the BB in lookout. There have been a few times the whole crew doesn't get in, some strange hic-up in game that I've reported more than once...
As far as going it solo, no, not an option anymore. You can however just invite a friend to crew up with you and go, and ask your friend to just hang out on the ship with you while you do all the work. Tha's about as solo as you can get right now.
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