My current boat is a 36 GB classic woodie. This was a boat I saw in the 70's and over the years continued to want. How did I settle on size, could have gone 42, thought about it.
I had a 35 & 37, a very comfortable 30 all of which were great for a couple but without 2nd couple sleeping except in the Saloon.
The Tri cabin layout worked for my plans because;
1) We had a couple that would change their plans and often came with us, that has changed, so far just once in three years, we all are aging out
2) Everyone I know has asked for a ride on the new boat, but none were available on my timetable. I am not about to work on their schedule.
3) 36 is adequate for two of us because we do not live aboard, a 40-42 in that case.
4) moorage is cheaper on a 36 than a 42 and it does not make sense to pay extra for a little more comfort with our current cruising being weekend, week at a time or even two weeks occasionally.
5) less than 36 no longer seems comfortable enough for the two us and we do not want to sleep in the V berth.
Bowball I mention this because I think you are nuts or have too much money to buy a large boat to entertain friends & family and maybe sell in 2 years taking a financial hit for your efforts. (No offense meant)