My boat ownership experience is somewhat unusual I would think. But it worked out fine, perhaps a lot of luck.
My college roomate asked me to help him with spring prep and a 31 foot sloop. I know absolutely nothing about boats. He then offered me the reward of sailing to his mooring (100 miles - 2 days). I loved it.
In the Fall he asked me if I wanted to get into a boat share with him. I, of course, sail I knew nothing and had to learn but loved the idea. He said he would teach me. We went to see the boat he had in mind. It was a 48' ketch - magnificent.
I had no idea of the issues of scale, but assumed he knew what he was doing and obviously someone sailed this large yachts. Why not us?
I then set about to read everything I could about sailing, cruising, yacht design, even boat partnerships and in the Spring took a Colgate sailing course. I was psyched.
His GF nixed the deal because she didn't want to share the boat. I was bummed. I went to the broker on my own and asked is he has something smaller by the same builder. He did. It was a new Contest 36. I told him that one day I wanted to go offshore etc. He said the boat could do it. I got a surveyor who told me the same, but it needed a lot of upgrades for offshore work.
I bought the boat and still own it. I spent the first 6 years sailing like crazy. Sailed whenever I could, in every condition including in a fall snowfall. Now that was weird.
I spent those 6 years upgrading the boat. Added a roller furler, windlass then an electric windlass, beefed up the electrical system, added a below decks autopilot, refrigeration, solar panels, Espar heating, inner forstay, storm canvas, assym chute, solid vang, dodger, instruments, pole and all sorts of deck hardware, running backs, new stanchion bases. The list of work and upgrades was endless and took 6 years... and probably cost half of what I paid for the new boat.
In '91 I was ready to go offshore and did the Marion Bermuda. Of course I had a crew and some good sailors including the broker who sold me the boat! We did fine, the boat performed well. I was ready and in the Fall left for 4 yrs of living aboard and cruising in the Caribbean. I was single handing and shorthanding the entire time, except for the first sail down to Antigua when I had 3 others with me.
I have continued to upgrade since then and almost everything but the hull, spars, engine, steering and cabinet work has been replaced and or upgraded. New hatches and ports, cushion covers, cockpit cushions, life lines, dodger.
I've done ALL the work myself, sometimes with the assistance and advice of a professional. What a learning experience! But I know the boat down to the last screw. For me it's the only way I feel safe and confident. No mysteries there.
And it's a never ending maintenance and upgrade operation. It's what I like more than anything.. messing about on boats.
I was lucky that the boat I started with is a great boat for MY purposes. It was solidly built, well design, very large sensible interior with great headroom, gorgeous teak joinery and comfy dry cockpit. It is single-handable for even an older person, though the 440 SF full battened main is pretty heavy to lift and the anchor with all chain is a back breaker.
And as SD points out in his reference to Beth... even with this size yacht the forces can get up there and "dangerous". I don't know that I would feel as secure sailing a larger yacht in heavy weather / conditions. This even applies to docking. I can do it all alone. This gives me freedom because I don't have to rely on crew to use and enjoy the boat.
Anchoring is no harder than parallel parking. If I need to move, I do it. If the water tanks are low, I pop over to the dock.
Yet the boat was comfy enough to live on without many "sacrifices". I have all the creature comforts, a huge galley, oodles of storage space, a huge nav station. shower, a separate aft cabin and a V for the occasional guests, a huge cockpit which can easily accommodate 8 people, but why would I want that?
Larger boats are nice for comfort and even for faster passages. But the latter is rather marginal and in my opinion offset by the downside of increased expenses and so forth.
However my main is about the size of a 40' masthead rig and so that would be the max size I think I would go for. The 40s I've seen are often no larger on the interior with the same 3 cabin layout and some, such as Hinkley are smaller!
My 36s is a brilliant design which I had nothing to do with. But it proved to me that this was more than adequate to sail offshore and live comfortably on. I was lucky 21 yrs ago... and I still benefit from that twist of fate.
Think about it and look around before you jump.