Hey JB,
As far as the outriggers: I think the wishbones are more desirable for a serious - hardcore, frequent fisherman, not sure why though. I want to install the hard-top Taco's on my new (to me) 330 Express. I had the Lee wishbones on my 282 Sailfish. The wishbones are more in the way when you are trying to get to the front of the boat, which is every time you use it. In addition, I had to take them down due to the height when going under certain bridges. The hard top mounted outriggers will do the job of spreading your lines when you fish like this, are never in the way, and don't have to be removed to go under lower bridges. Cruising to Long Island: I am planning, for the first time, to do the Montauk, Block Island run this summer, so I do not have good suggestions, but would be happy to report what I find out (I have friends that have done this yearly). From what I understand, there is only 1 or 2 places to even tie up in Block, so the decision is made for you. I fish/cruise further to the west. If you were willing to go a little further, I have a couple of great recommendations on Fire Island. Family friendly communities, only accesable by boat, and family oriented marinas. 2 I am very familiar with are Ocean Beach (the community) and Atlantic (the marina). There are no cars and many kids, so playgrounds, ice cream shops and candy stores are always buzzing. In addition there are great restuarants and bars (candy stores for the adults). The fishing is better out east (the gut between block and montauk), but it ain't bad here. I'd be happy to share more as the summer draws near.