Shavdog,
Some of the "negative features" of my 37.5 are as follows:
I would have to say that the below decks in my 37.5 can be a bit dark with the smaller port holes. My step son is 6'4" and cannot stand upright below. Also, the aft cabin although a centerline queen berth is a bit like sleeping in cave. I have a 10 inch mattress which leaves just enough clearance to turn while sleeping. At the beginning of each season, i log about 10 head bonks and 10 elbow bonks on the "ceiling" while sleeping until I re-orient. My legend does not have a swim platform, just a ladder and a slanted stern. Initially I liked this for following seas, but.....it is a nuisance to get on and off the boat.
I have 75 gallon fresh water, 25 gal waste and 35 gal diesel. The boat sails so well, I have only spent $54 in diesel in three seasons.
The 376 is similar weight and displacement and most likely has similar sailing characteristics. I agree with John Murphy.....i sail constantly, even when other are at the dock in light Chesapeake winds. In fact, my bets days have been in July and August. I think the 376 may be more spacious and light down below, and has better accommodations than the 37.5.
One last thing, my 37.5 doesn't have a separate stall shower, so when we shower the whole head gets wet. The boats you're looking at are 5 years younger than mine. I suspect things have improved greatly in the 5 years.
I wanted to give you an honest opinion of the negatives of the 37.5 as well as the positives. I most certainly mean no disrespect to John and his 376. That is a great boat. It is a tough choice. For me, it came down to which boat I felt was maintained better, and the 37.5 was the best maintained of the ones I saw. Incidentally, I had to add a 100 amp alternator, a fridge system, and a wheel pilot since she had none of the above. Also, no A/C, and no electric windlass. I use two small stand up portables down below when at a marina.
Good luck!