A philosopher once said, "don't live in the answers but seek the questions." Having done what I think you want to do four years ago--find a boat I could sail at seventy-seven by myself--here are some questions you might want to ask yourself. They were what I needed to know...
What size boat did I feel comfortable in? I wanted something smaller then my H380 (which I could single hand but I tired easily) and I selected a Hunter 27 from among a number of candidates. One (of many reasons) for the Hunter was that all controls came back to the cockpit and all the running lines (sheets and traveler) came to the helm. I don't have to move much around the cockpit.
Running out of muscles, I elected to go with roller furling main and jib. I was fortunate that just after I bought my boat the WinchRite (see: Shop this web) was introduced. Best thing for me ever as I have an aneurism on my heart.
I also added a Raymarine autopilot. It helps me tack--actually it is a rather cool device. Hit two buttons simultaneously and it begins a tack and I can release one jib sheet and bring in the other jib sheet. We're a team, Ray and I.
Now that I could control the boat under sail how could I control the boat when not sailing. It came with a great little diesel to which I added a three bladed Max prop. Now I could go forward, backward, turn on a dime all from the helm. No need for bow power. Indeed, I back into my slip as much as come into it in forward.
But the slip scared me a bit. Could I see well enough NOT to hit the dock. I didn't think so so I lined the slip with Nomar dock fenders. This did two things--first, I don't have to deploy fenders every time I return to the slip meaning I stay in the cockpit. Second, I don't loose my cool when I do hit the dock--no harm done.
I also rigged cleats on my near aft stanchions to which when going sailing I attached by bow lines so when I return to the slip I need only to get a stern line and my bow line which is nearby. Tell me if this doesn't make sense. But i wanted to control the boat when coming into the slip.
So for me I answered the question of how to control the boat under sail and the other question of how to control the boat under power and in the slip.
Then i asked the question, "what would make me feel good?" OR what did I need. I needed a marine head. I don't have the strength to lug around a porta-potty. I also wanted a bunk that I could take a nap. I find I use my boat at the dock as much as I sail. With that in mind I wanted a decent stereo--Hunter supplied that with the boat. I'm pleased with that aspect. I also added companionway doors (see them on sale now on this web site) so that I didn't have to fuss with those damnable hatch boards. What a delight they are and they really fit the boat in style and looks.
I also had added a Webasto force air furnace (their smallest) and it has been a total delight. Even after coming in from sailing I sometimes turn it on to warm me up--apparently my own thermostat doesn't work as well anymore.
I also bought Bottom Siders from this site. My tush ain't what it use to be and comfort was important.
I also bought ST 60 Raymaine sailing instruments. At that time they were the largest in viewing size and in sunlight. Easy on my eyes.
I also bought two plastic glasses from this site that exactly fit cup holders just behind the helm station next to the tourist seats. They have been invaluable keeping tea hot or cold. Little things like that are important if you're going out sailing by yourself.
To continue answering the question, "what do I need?" I did get shore power and two ABS batteries so that I don't have to bend over and try to find the water level. Inside a wet cell is black on black, not my best viewing.
So I answered my questions. I've now have had the boat starting on it's fourth year. The question probably ought to be, "How did it all work out"
Although the boat is much smaller then my previous H380 it still had as much free board so my jumping down at the dock is still not comfortable. I missed up on this one. But since I back in much of the time, stepping off is not a problem-only when I come in bow first and have to get to the dock.
I put on a top of the line GPS (Garmin) which works find but I really could have used a hand held at best. I'm day sailing in an area I know. I also over did the VHF radio. A good ICOM hand held that I already had was good enough. These two items were a waste of money. I was also fascinated of how much stuff I didn't need....tools (I use a Leatherman as much as anything), storage areas, books (I now use a Kindle), fenders (I now use blow ups as they save much space)....it was a major change in my thinking; what do I need just to go sailing? I also added LED lights for the navigation locker except I don't sail in the dark anymore. I come home to hot food and my bed.
Would I do anything different? Probably not. I haven't seen a boat that I like better then the one I have now. It works for me. It's small and I feel comfortable in it and sailing it--that's my criteria.
But I also give my little boat credit--I think I'm a better person physically and mentally because of it. I have enough medical problems that could wear me down but I want to go sailing first. I feel stressed.....so I go down to the boat and just read and drink my tea. Somedays I just go down and listen to music. Very soothing....and as I've said on another web site, I need soothing either under sail or on the dock. I'm going to be sailing when I'm in my eighties.
I wish you well.