I dunnno I used to feel confident taking a 1971 19' Silverline W/115 Mercury about the same vintage to the BB bouy from Bass River. I DO NOT recomend this to anyone. I picked my day and went out with a group of others, everything went ok good. Now looking back I would never do anything like that again. As for the southside in the sound I am in the process of obtaning a 20' SeaCraft CC power is undecided yet I may go small 115 Evinrude or go with an older 175 Mercury BlackMax, Either way it will be capable. I would feel comfortable around the sound and on the outside (whithin 15 miles) on a normal day. For shelterd waters I will be using the other boat a 20' PennYan Tunnel drive. It will work out in the bay but i wouldn't take it outside too far, it doesnt have enough bite on the water to push it up a wave if need be. I would feel comfortable taking either or out past stellwagen on the right day tho. On the otherhand I have friends that have extremely reliable and capable boats that piss themselves when going beyond the sight of land.
In the long and short it is all what you are willing to put up with and what you can not. if you do not mind a wet pounding ride go small and fast, if you like smooth and moderate speed, go large.
