We spent a month cruising on an older Willard 40 sedan in the PNW. Even without stabilization it felt very sure-footed in a blow in the Georgia/Malaspina straights. Comfortable rolling motion. Space utilization was good. Biggest downside was engine access. Almost impossible for a tall person to work around the engine with only about 3 feet of headroom. I understand the pilot house version has better engine access.
Actually, the PH version does not have better access. I personally like the ER on the W40s, though concede this compares to other boats in the class that do not have stand-up ERs (including the KK42). W40's have a mid-ship thwart fuel tank vs twin saddle tanks that are common on boats in this size/class. This has a number of benefits. First, a buffer between the ER and sleeping quarters. Second, balanced ride as fuel is consumed. Finally, ER is wide-open with plenty of room for gear, including a Splendide clothes washer if desired. I'm not quite 6-foot tall and find the W40 ER comfortable to work in in a seated position.
The W40 is a relatively small 40-footer with a modest beam and canoe stern. But what a boat she is. Attractive lines, 2000 nm range at under 2gph/7-kts, and very comfortable ride. Accommodations are not fancy, but more than adequate for a couple with occasional guests. My only demerit for them is I'm not a fan of cored decks (KK42s are similar). Depending on how she's equipped - if still has mast/boom, air-draft may be an issue for the Loop.
But I agree with Eric - while I'd definitely chose a W40 for The Loop, I am a solid Willard fan, having owned two (current W36 and prior W30) for the past 25+ years and still loving the boats. But I'd have to set aside my bias and ask folks what they are trying to accomplish with the boat. My wife and I cruised the Sacramento Delta for weeks at a time and really liked the jogging-speed pace of a full-displacement boat. We also loved the protected running gear - I would not own a boat again without well-protected running gear.
To the OP - if you're looking at Adria, one of the last W40's built around 1999, she's reportedly a fine example that has been owned for 15+ years by a very knowledgeable owner who also owned a W30 before her. Great example that has been stored in a climate controlled warehouse each winter so is likely in exceptional condition.
https://www.yachtworld.com/boats/1999/willard-40-3617588/
If you're looking at Lilliana, a 1978 W40 located in the San Carlos MX (top of Sea of Cortez, several hour drive south of Arizona), she's been owned by another owner with a lot of experience. Current owner also cruises a W30 in southern Alaska. This owner happens to be a 3-boat owner - he sails a vintage 35-foot sailboat on SF Bay. To say he's knowledgeable is an understatement.
https://www.yachtworld.com/boats/1978/willard-40-fbs-3847758/
Personally, I prefer the sedan layout to the PH layout. These are both good examples.
Good luck - and feel free to join the Willard Boat Owners Group at
https://willardboatowners.groups.io/g/main. Owners and/or lookers are always welcomed.
Peter
(co-moderator Willard Boat Owners group)