A competent couple can handle a 58' no problem. I've run 70's, 80's and even a 90' with just myself and a mate. And 4'6" is no big deal either. Under 5' is fine for running around in SW FL or the Bahamas.
Many people start with a smaller boat and quickly find they want/need more room. So looking at something bigger than 37' is not unreasonable.
I would suggest chartering a few different size boats to get a better feel for what you think you need.
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