Hmm. I have a 32' yacht which I sail alone. I am also retired and cannot jump mountains or anything near that.
That size is ok but not comfortable particularly when you have to stow spare sails etc.
Add another person (which in my case is unlikely but nevertheless one prefers to keep the possibility alive) and it is ok at least to my mind but not comfortable.
I kinda wonder how much experience you have.
Going into a dock
with the main up seems a bit hairy as a general rule
On the other hand I agree that raising and lowering the main singlehanded can be anxiety provoking.
Desirably one could do this from the cockpit
, however I am a bit sceptical about this. It would be ok with a well thought out system and an autopilot
. Holding the boat to windward can be an issue even with a novice
crew (how do I tell which way the wind
is blowing from and which way do I turn the tiller?)
The boat can also be bouncing about so you need handholds, even maybe granny bars.
Probably more importantly you need a flaking system, which is cheap
to rig yourself - lazy jacks (took a while to remember the term).
My suspicion is you need more time on the water
as well as finding ways to make it easy on yourself - like an electric
capstan. You will of course have more free time to wait out weather
. deep reefs
to make it easier etc.