So true. You can make all the lists you want and read all the books you want and kick all the tires, but until you've really spent time sailing and living on at least one boat, you'll have no idea what is important to you in a boat. Unless you're one of those people that's easily appeased and doesn't second guess everything, in which case, I'm jealous.
I suspect the PO is not one of those people, otherwise he/she wouldn't have started this thread.
In most of India, arranged marriage is the norm. Your wife/husband is your first everything. That is your official marriage.
But there is a whole system of classifies and websites for what are called "love marriages". That is where you find what you actually want. I think boats are the same.
(apologies in advance to anyone who finds offense in that analogy)
The boat I own I bought new in 1985. I was 38 yrs old and essentially no sailing experience save for a learn to sail course, and some time on a friend's boat the summer before I bout the 36s. Yes I had read everything I could. Friend was very knowledgeable and advised/mentored me.
I am an architect so perhaps I can look at "spaces/function" differently than the average person. I don't know.
The 36s looked fabulous to me, intimidating for sure... but it turned out to be... in my opinion almost the perfect boat for me. I've sailed it 10's of thousands of miles... coastal, offshore, live aboard and mostly single and short handed (one other).
The boat from the factory lacked many things needed for live aboard and offshore work. I spent 6 years and lots of money upgrading the new boat. And I've spend that amount x 2 or 3 over the years in further upgrades. Of course I've gone through several suits of sails, running rigging, upgraded the blocks and so forth. Added an electric windlass, engine drive refer, forced air diesel heat, several generations of nav instruments/electronics/radios. Added an AP, Re-did the lifelines, added an inner forestay and trysail track, upgraded and added winches, solar, completely re did the 12 electrics - wiring, switches, batts. Did a bunch or joinery upgrades, changed the head, replaced the hatches and all the port lites, upholstery a few times.
The boat had what to me is a very successful design... good bones and all I did was make it fit my sailing / live aboard needs.
I would not do this again... even knowing what I do from over 3 decades of sailing.
Whether it was luck, or skill and hard work... or both... what I did is proof that someone can get the right boat the first time but it STILL NEEDS to be "tailored" to the individual who owns it. Some people accept poorly fit clothes... others don't.
There are many things you can "change" on a boat. Many things you cannot.
You need to be smart enough, talented enough, stupid enough, and persistent enough and of course lucky enough to make it work on the first buy.