First consideration should be safety for yourself and other boaters. Single handing adds additional risks such as if you have a heart attack or you go below on autopilot and the duration causes you to cross commercial shipping lanes which exist in any major body of water and locations where bays exit to oceans. Other factors to safety are your local geography where you sail, for instance if you sail in the north end of the chesapeake bay you want a shallower keel that is you are in the southern bay, if you sail the Columbia River, the bar at exit to ocean is very treacherous even at slack tide. For all of these safety considerations there are mitigations for a single hander, such as top mast quality VHF coms, mid mast radar reflector, jack lines that are convenient, reliable maintenance of your auxilary, quality fuel filters that can be visually checked easily, flare guns easily available, communication plan, always let someone know where you generally will be sailing and what time you will be back and you call them when you return, this can be a friend or the marina office. Always wear a life jacket that has a strobe if alone. Have good condition and oversized ground tackle, nothing worse than a soft mud bottom and a small "lunch" danforth that drags and you hit some else while below. This has never happened to me, because I stay above until I am sure the anchor cannot be dragged.My experience has been very small sailboats or 30 ft with another person years ago.
Now retired and divorced I'm looking at something 30 -35 ft that can be sailed alone. I'm thinking I'd need a roller furloughing genoa, maybe also a jib and then some kind of auto pilot or what I rememberer as a tiller tamer. Raising the main is no issue if the lines come back to the coxpit but the fore sail I think is an issue especially when you bring it down and it tends to fall over the side and you have to go forward and retrieve it onto the deck. Did I get that right?
So I've been looking at boats that have an autopilot where I thought I could set it and if necessary go forward or down below to grab a sandwich. Now my sailing will probably be on the Columbia river in Oregon so the need to tack back and forth, short tacks, will be and issue.
I've looked a a few boats mainly with the furloughing genoa because of the above but I found one with the normal jib/genoa and was wondering if that could still work or would I have to purchase a furloughing genoa and some kind of autopilot etc??
These may all be second nature to you, hopefully advice not needed, but it is very important to understand that a friend aboard is always a good safety practice until you are 100% sure you are capable and setup to address anything that nature throws at you.
Just my 2 Cents!
D. A. Davis