I may be wrong here, but I guessed he was looking for an inland lake type boat...he said bowrider or cuddy, which leads me to think more of a sport-boat or ski boat type rather than anything that says Boston Whaler or Grady White on it. Those may well hold excellent value in comparison, but I think he is looking more to the sporty-boat area.
I am a Craigslist junkie, and have shopped for (used) boats pretty much continuously for the past four years. What I have noticed, using both regional (South East TN, and 250 mile radius) and some national searches (Ebay, Craigslist, BoatTrader, Facebook Marketplace) is that different boats hold value better in different regions. This has been stated before I know. Fishing boats like the Whaler and Grady do well near coastal or large inland lakes where 19-23' sport boats are a dime a dozen. In my area, (again, the SE USA) a Whaler or Grady would be all but useless, and make better fish restaurant road side signage than anything else. In shopping for a used 20-23' bowrider, this is what I found: Sea Ray, Four Winns, Donzi, Cobalt, Chris Craft, Bryant, Mariah, and Wellcraft all seem to bring higher prices and hold that price longer (when maintained or restored properly) and seem to be very popular. The lesser ones seem to be Bayliner, Maxum, Tahoe, Regal, Chapparal, and Larson. Some of these may still be popular (there are Bayliners EVERYWHERE) and may even be good boats, but when equally appointed and powered and in equal condition, they will not bring the same money as the "top tier" boats. In purpose built boats in that size, Mastercraft is the runaway favorite, and holds its value far better than Malibu, Supra, Tige, Centurion, or even Nautique. All of which may be great boats, and are all VERY expensive, but nothing can bring the resale of a Mastercraft.
Hope this helps. Not meaning to offend anyone if you own a Bayliner or such, just listing my personal observations from for sale listings over the past few years.