I sailed over 7,000 miles in the South Pacific and home to San Francisco with my 2 children, which other singlehanders call half handing. We had a 44ft steel ketch an Endurance.
Some men were rats and some admired me. The nice thing about sailing is if you don''t like your neighbor you can just pick up the hook and move. We buddy boated with other families and other single handing men, and sometimes sailed alone. So there is a great variety. I did most of the engine work myself, which I admit is a challenge, but good maintenance prevents a lot of the work and also if you have a diesel engine remember to let it do some work, because lack of use is worse than too much use.
I definitely loved my roller furling foresail, for quick and easy reefing. I had a self tending stay sail which was also great. You can see a picture of EASY on my personal page. 44 feet is a bit too big for me, I am only 5 feet 2, but that was what I had, so that is what I dealt with. 40 feet would have been perfect.
I had a troublesome Autohelm which finally became beyond repair and we used the Aires wind vane even under motor. I have no preference to wheel or tiller. Tiller is easier to bungy cord and rig self steering. The Aires was my best crew!
If you have any other questions I love nothing more than to talk sailing.