I am not aware of any design flaw in the CONQUEST 21 nor of any particular "reputation" associated with it, other than being a Boston Whaler boat and inheriting all of those reputations, true and false, that accompany a Boston Whaler boat.
I do observe that the decade of the 1990's was a very unusual period in the history of Boston Whaler. Let me give a time line of which company owned Boston Whaler in this era:
1989 to 1993: Reebok Shoe
1994 to 1996: Meridian Sports
1996 to present: Brunswick, Inc.
The Reebok shoe company owner and the Meridian ski-boat owner were probably not a good fit for Boston Whaler, a conclusion supported by the very short tenure of each of their ownerships.
My inference from the three changes in ownership: the 1990's were a rather turbulent decade for Boston Whaler and its employees.
In particular, the head designer of Boston Whaler boats at the beginning of the decade was Peter Van Lancker, replacing the long-serving Bob Dougherty who was forced out in a rather unceremonious very fast exit one day quite by surprise. There was also some design influence from SeaRay boats.
Van Lancker left in 1996, and a team of designers seemed to be in place who I presume produced the Accutrack (sometimes AccuTrack) hull.
So during the 1990's Boston Whaler was producing hulls with four significantly different designs: the classic vestigial twin-sponsor round-bottom hulls (Fisher and odd-number model lengths 9, 11, 13, 15, 17) , the classic vestigial twin-sponsor moderate V-bottom hulls (Dougherty and even-number model lengths 18, 20, 22, 24/25 along with the biggeer 25 and 27 hulls), the sharper and deeper V-hulls with straight transoms of Van Lancker (which never seemed to merit a special naming but were seen in the 21-foot and 23-foot OUTRAGE and WALKAROUND hulls), and the reverse transom Accutrack hulls (seen in the CONQUEST 21 and others) from what seems to be a team of designers.
Also in this decade the main production site moved to Edgewater, Florida, from Massachusetts, which likely resulted in an influx of new production workers, although many key people stayed on and moved to Florida from Massachusetts.
The arrival of Brunswick as owner of Boston Whaler in 1996 began the move to mandatory tie-in sales of Mercury engines, which resulted in many long-time Boston Whaler dealers being forced out due to association with other engine brands and lack of un-rigged boats from the factory.
The CONQUEST 21 model was among the first to feature the reversed-slope "Euro-transom" look, use an Accutrack hull, be built in Florida, and to be sold with a mandatory tie-in of a Mercury outboard engine. With an eye to those factors, one might infer that sales of this model might have been facing some obstacles from traditional Boston Whaler buyers.
For more details on the history of ownership, see my article
The Boston Whaler Companyhttp://continuouswave.com/whaler/reference/history/whaler.htmlRegarding the influence of Peter Van Lancker on Boston Whaler, his c.v. from his
LinkedIn page shows:
1984 to 1989, Black Watch Boats, President
1989 to 1996, Boston Whaler, VP Engineering and Design
1996 to 2001, Outboard Marine Company (OMC) VP Boat Group Engineering and Design
2001 to present, Hunt Yachts, President
That is my thinking, based on facts and reasonable conclusions from those facts. There is lots of "dock talk" about boats that is passed around by boaters, but I find that often those folks are misinformed.