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.