In terms of coming and going I personally would not give it much worry. First you do not have to clear out of Bahama when going back to US, second, US simply asks where you came from upon clearing in. You get no passport stamp or anything coming back into US and when you head back to Bahamas you do not need to clear out of the US So..back in the Bahama would be as if you never left.
In terms of the "crossing", don't over think it. In my opinion it is not even a real "passage", but rather a long day sail. The gulf stream is no big spit except with strong north winds and wave. As for weather window with an E-35 I would not hesitate to leave with a two day wind wave of 25-30kt and 3-4 meter seas if from anything south of east or west (just not on the nose or from the north)
You can trust the new explorer charts. The "not for navigation" is only because the US is infected with the "attorney virus"
After sailing a couple years in the Med., the entire eastern Caribbean, we found going through the Bahamas, especially the far islands, fantastic. So much so we have decided to head back next month and spend 4 months before heading back down the chain to the ABC's. They Bahama islands south are fantastic!
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