Before I was married, I singlehanded my 40' 28,000 lb Creekmore 40. I'd say the hardest part on a larger vessel is docking
and getting the ground tackle up (without an electric
windlass). It's very important to plan your actions before you do them. Have all lines ready to go at all times.
I don't think a furling
main ever crossed my mind. Full battens and lazy jacks are the way to go.
Hank on jib
wasn't too bad either. The worst part was changing jibs offshore
when it was rough.
Usually I just dropped and secured the jib
and sailed under reefed main and staysail. The roller furling
does get the sail out of the way when anchoring
A good autopilot
is important. A windvane
is nice to have too but often can't be set up in an instant.
A vessel that balances easily makes things much easier. Before I had an autopilot
I could let go of the helm
for long periods of time and she'd sail straight.
You will never find single
line reefing on any boat I own.
These days I have an electric windlass
, roller furling
, and a wonderful wife (who used to be a singlehander herself).