I would think a sail boat could get you into more trouble. Maybe I am wrong.
Either way. Money and trouble seem to have a hands in affect.
I see very nice vehicals in slips sitting. I hang around a week or so. Come back the next month. The same very large boat to me is still sitting.
I would guess these monsters are taken out a few times a year. The operators can not be that experianced.
There is only one way to get experiance. They do not teach it in any class, but classes seem to help.