Given what dunces are selling the sailing lyfestyle on youtube, it can't be too hard for the average KC member. If you have enough money for gas, you can always motor when the wind isn't blowing the right way.
Key aspects are knot tying knowledge, boat knowledge and general organization, like with checklists for everything. Navigation is kinda worthless given that you gonna have GPS and detailed water maps.
I'd try to get to know basic aspects of yachtbuilding, like materials, how structural integrity is generated, upkeep and maintenance, etc. Read on forums what people recommend and like.
From what I have gathered steel boats are much more forgiving than fiber glass, but require a similar amount of upkeep. Where a rustbucket gets a dent, a fiber glass boat is completely fucked. Than again you have to worry about galvanization, rust and the boats tend to be slower.
http://www.kastenmarine.com/articles.htm
https://www.cruisersforum.com/forums/f47/steel-boat-heaven-or-hell-170179.html
Lastly a big point is how independent you want to be and if there'll be other people. 12V battery system, solar panels charging it and a reverse osmosis system + freezer running on 12V are kinda needed if you want to stay off grid for longer than a month. Corona hasn't made things easier as well. You can't even go into marinas half the time and are lucky if you get supplied on the water before being forced to fuck off.