I too would like to buy a boat, I also like traditional styled boats, and I plan to liveaboard
Since your wife wants the "Captain Ron" look, you might find something appealing in the Taiwanese boats built in the 1970s and 1980s, when the use of wood, teak
interiors and trim and decks, and "traditional styling" was the fad or fashion. Many of those boats, by different builders were built and are still sailing. Many or most will likely need serious upgrades to make them safe for long voyages, but most would be suitable for a more sedentary liveaboard
life and coastal cruising.
When you search sites like sailboatlistings(dotcom) or boattrader(dotcom) or yachtworld(dotcom) you might enjoy looking at boats like:
CT41. (CT or Ta Chiao) is the brand or maker name). Here is an example now for sale
1973 Ta Chiao CT 41 CT41 sailboat for sale in Florida
Tatyana 37. (Sometimes called a Ta Chiao 37)
Hans Christian (probably the most highly priced boats on this list)
There were many boats built in the USA that used teak trim and interiors and traditional styling to appeal to the public.
The most commonly seen is probably the Westsail brand.
Westsail 32, 43
Since you like the pilothouse look on that Landfall 39, you might also like the Islander Freeport
41 boats. They are from the same era, priced about the same, and they have a nice aft cabin
with good big double berth/bed for the grandparents and many portlights
(Windows) to let in light and air.
Here is a single
website that has drawings, articles, and data n many boats of that era and type. If you have not yet seen this site, I suspect you and others will enjoy it. It is a very good site for learning
about many boats of that era (1980s) and their stories and builds and sizes..bluewaterboats(dot)org
Full List of Sailboats
Good luck on your search and future sailing!