Good points..... but, for a liveaboard, I'd rather start with the largest possible and learn that, then when that phase is behind me, we have the space for comfortable living.
When we had the 50 foot GulfStar, as large as that was, when we were in the main salon, there was only a relatively small area between the opposing settee and couch to walk through. So, when we both wanted to move / walk, it was a tight maneuver to walk past each other. The boat we have now has an open floor space, which is large enough to dance upon.
As far as the amount of time it takes to raise or lower the sails, well, there might be a few seconds more time to raise each of them, just because they are a bit higher, but I'm not in the Americas Cup racing, so a few seconds isn't anything of value to me.
I still have one halyard for one sail, and a pair of sheets per forward sail(s).
I haven't noticed any additional hassles or time to deploy those, or furl them either. It is the same configuration, the same lines, just slightly longer, and or, slightly larger all the way around.
As far as docking, the bigger the boat, as I have experienced, the smoother she pulls into or leaves a dock. This boat is 65,000 lbs., with a full keel and a 135 hp Ford Lehman. It has hydraulic steering too. As I learned a long time ago, for dock maneuvers, go as slow as you can, and with this larger boat, the currents and wind have a much lower influence on the boat when docking. Clearly a lighter boat will be more easily affected by those influences. This one is like a slow moving train, which requires a lot more energy to make it deviate from where I am directing her to go.
As far as keeping her "simple", from the key in the ignition to the throttle / shifter controls, to the lines / sheets, and the navigation equipment, all of these I had in a smaller boat, and are neither new things to deal with, nor are they any more involved than the smaller boat ones. Depth, wind velocity / direction, auto helm, SOG, etc., are the same issues regardless of size.
And, if I have a bigger "family" onboard, everyone is out of the way, more often than not, instead of having to be directed where to sit, or where to go.
More space will require more sandpaper and varnish, without any argument.
Longer wires if you need to add a device are required, larger tanks to clean, bigger sheets for the bigger beds, larger tables to wipe down, larger shower stalls to wash the walls of, bigger floor space to vacuum or mop, more windows and port lights to clean, bigger couches to fluff the pillows on, and all the other slightly greater tasks involved with a larger living space are unarguably more not less laborious. But, do I really mind having to vacuum or mop more than a small walk way so much that I don't like a spacious floor plan? Really? No, I like having the space and have never minded maintaining it.
Even maintaining the engine is basically the same. There is one oil filter, one input and return fuel line, etc., though it does contain more oil.... and instead of one gallon per hour this runs 2 gallons per hour, including the 8 kw diesel generator.... not a real problem, considering I generally run the motr for about 1 hour at the most from the dock until I raise the larger sails, and then press the same size engine kill button to turn that off....
It isn't any more complex than the smaller one, just stronger, and bigger.
What I have already mentioned is not a "plus" vs a smaller sailboat is the amount of low wind speed, and maneuverability. A large displacement boat requires more wind to move along, requires more space to turn around in, and is clearly not as "nimble".
I could also mention that it requires bigger waves to rock us! I have been delighted by the fact that when a motor boat goes flying by me, I am barely affected!!!! Cool, VERY cool!
So, all in all, my "family" is more comfortable, and less bounced around, not to mention SAFER since they are less likely to break a rib by being thrown around, or worse yet, thrown overboard.
Come on out with me, and note how relaxing it is being able to really stretch out, and remain that way while you read a book, or just watch the waves go by the hull.
This isn't camping out, this is comfortable relaxing living; and isn't that what a liveaborad should be?