Agree your $100 bet would be very safe.
The quarter tonner suggestion is tops - in Europe they have revived the class as here and many other links...they were offshore and overnight capable and the 2 crew would be certainly challenged but it could be done unless the 1978 1/4 ton cup weather in Japan was repeated. At that event there were masts over the side and boats capsizing like dinghys.............albeit they were the limit of the IOR centreboard yacht design days........nothing against lift keel yachts but they certainly pushed the envelope then.............the ballast ratio was way too small.........
https://www.sail-world.com/news/218429/Quarter-Ton-Cup-2019-day-1rbsailing.blogspot.com/2015/09/quarter-ton-cup-1978.htmlSomeone is trying to do a similar revival here;
www.aussietonyachts.com.au/For a cost effective current build yacht would suggest the SB20 but it might be considered too small.........Tony Castro is a brilliant designer...
en.wikipedia.org/wiki/SB20For a bit bigger would suggest one of the smaller J boats.............or Melges 24.............or many others not more than 8m say........