The demographic of startup founders is severely lacking in gender and racial diversity. I don't know if I would want to go for months only seeing 1000 similar people (mostly men) with very similar occupations. In the end, entrepreneurs are people too and this would be a very bizarre society.
You can go on "shore leave" as often as a US tourist visa allows. I recall having read in a previous mention of Blueseed that they could set up connections to ports in Mexico and Canada as well, although I'm not perfectly sure how that would work - a ferry would take a long time. Seaplanes perhaps?
And as often as your wallet can afford the trip --- travel by boat isn't cheap. I noticed that they didn't mention the cost of the boat taxi; either it is a free shuttle, partially subsidized, or in worst case you'll cover the actual cost of the boat trip (a ferry in Seattle cost me $20 one way when I was there years ago; gas prices have gone up since, boats get horrible mileage, and they depreciate quickly and need lots of upkeep in salt water).
I'm male but both my cofounders are female. One of whom is not a US citizen and thus to be in "silicon valley" this "boat" would be the best option for us.
Here in Startup Chile, a lot of the companies are run by women or involve women-- I'd say the gender ratio (completely unscientific) is something like %60 men, not %90 men.