A floppy-roller trailer is unsuitable for use with any Boston Whaler boat due to the nature of the Unibond hull.
The best trailer set up is to use a combination of keel rollers to support most of the weight of the hull, and outward bunks to stabilize the hull. However, there is usually not a trailer on the market these days with those features.
A compromise is to use a bunk trailer but one with a set of inner bunks located close to the keel to support the hull weight and outer bunks to stabilize the hull.
While the original c.1970 advice strongly recommended using keel roller trailers, Boston Whaler has been delivering its newer boats on bunk trailers. For a 2005 255 CONQUEST, the bunk trailer is certainly the choice over a floppy-roller trailer.
The topic trailering is discussed in more detail in an article in the REFERENCE section. See
https://continuouswave.com/whaler/reference/trailering/For advice on fitting the trailer to the hull, see
Trailer Rigging For Boston Whaler Boatshttps://continuouswave.com/whaler/refer ... ailer.htmlThe load of a 255 CONQUEST may push the trailer into the three-axle variety. If buying a two-axle trailer, don't scrimp on the trailer load weight specifications. You may be surprised by the total weight of a 255 CONQUEST when on a trailer.