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I have a 2000 Whaler 17 and I have a Load Rite trailer with three keel rollers and and bunks on the side to balance the boat. I added CE smith 40” guides. This works well for me. Lots of information here about using a trailer with keel rollers with bunks being the preferred set up. I have to agree based on my 6 months expert with that. My trailer does not have a swing away tongue and I wish I had that. A drop foot Jack that I installed is nice and saves time but a wheeled Jack allows you to move the trailer of course.
I have a classic Montauk also, and in my opinion the VERY BEST trailer made for that boat is by Continental, Tilt-frame model CV-7 2000# capacity. All galvanized structural channel welded frame, keel roller design. I would recommend a 14" wheel upgrade. Be sure you order it with 12" Stoltz rollers with SS shafts. Side bunks should be 2 x 4 x 5' . This trailer fits a Montauk like it was specially designed for it, and launching/retrieval is a breeze.
I bought mine in SE Florida 10 years ago, and it cost $1200. Probably more like $1500 today, and I have heard delivery times are getting long. Continental has Dealers all over SE Florida, but I have heard Hub Trailer in West Palm Beach is very competitive. Don't let a dealer talk you out of this model. It's absolutely perfect for the hull.