I propose there should be a difficulty ratio applied to the ugliness in accordance with length.
edit: also a multiplier for a production boat, my suggestion below is an owner build.
i've seen many a <25' boat meet the ugliness criteria just for headroom and smaller = cheaper, i spotted one in the flesh the other day and was going to photo it for here until i got a pang of guilt after the owner showed me how to set up my cunningham, i just couldn't do it, he was a nice guy.
roberts 40' ?
Looks to me like a Van de Stadt .... maybe a 34 but more likely a Carribean 40 albeit much bastadised.