Re: Sailing alone??
Most nearly every post focuses on the physical ability to handle a boat. Seems to me that is putting horse before the cart. In order to safely sail solo it is important to be able to plan ahead. In order to do that you have to visualize what you re trying to do, predict how the boat will react to you inputs, and plan your escape route if all goes haywire. All of those things depend upon experience. If no experience, then you should restrict yourself to boats small enough that you can manhandle them if all goes haywire.
I used to single hand a 42' keel boat, from dock to dock. It was always a pleasure. Now we have a 38'cat. Fun sailing, but docking is challenging.
If your SO will allow, buy a simple old board boat or dinghy, sail in swim suits, regularly capsize and laugh about it, learn abut wind, waves, mistakes, etc. Sell the thing (or give it away) after a season, and then look for a real boat. You will be both happier, and a better sailor.