Should I have get a guide? Nah!

Snapperhead27,
Another cheap option would be buying a boat over 30 feet with a nice cabin and docking it out in Montauk. Summer Dock is easily over $5000 , the winter storage is way more reasonable. You could stay out there on the Boat for a week at a time and have a wonderful time out there. Me and my family kept our 27 foot cabin cruiser out in Snug Harbor Marina during the summer of 1972 and 1973. Almost every weekend we went out there and fished our brains out. Slept on the Boat, the Marina has bathrooms, Showers, a Pool. That could be your Condo.Beautiful Marina right across the road from Lake Montauk. That's what I would do if I wanted good fishing. I'd feel nervous having anything in the Keys. You could always buy a Condo down in Florida like in West Palm Beach or Fort Lauderdale at Century Village. Nice 1 bedroom Condo's for $75,000 and $500 HOA.
 

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